- Acid promoted metal free synthesis of triazole-fused heterocycles via intramolecular [3+2] cycloaddition
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A practical and efficient protocol for the synthesis of triazole-fused heterocycles through intramolecular metal free [3+2] azide-alkyne cycloaddition reaction is described. Range of acids was selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by acids gave fused triazoles including multivariate rings and heterocycles. Various fused triazoles and bistriazoles were obtained in good yields under mild reaction conditions.
- Zhang, Youlai,Wang, Mengdi,Li, Junru,Di, Qingtong,Tian, Ziye,Chen, Baoquan,Zhang, Huan,Tanimoto, Hiroki,Morimoto, Tsumoru,Kakiuchi, Kiyomi
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- Iridium complex-catalyzed [2+2+2] cycloaddition of α,ω-diynes with monoynes and monoenes
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[Ir(cod)Cl]2/DPPE was found to be a new catalyst for the cycloaddition of α,ω-diynes with monoynes to give polysubstituted benzene derivatives in high yields. Internal monoynes as well as terminal monoynes could be used. The reaction tolerates a broad range of functional groups such as alcohol, amine, alkene, ether, halogen, and nitrile. The reaction of 1,6-octadiyne derivatives with 1-alkynes gives ortho products and meta products. The regioselectivity could be controlled by the choice of ligand. The reaction with DPPE was meta selective, with meta selectivity of up to 82%. The reaction with DPPF was ortho selective, with ortho selectivity of up to 88%. We propose a mechanism to account for this regioseleetive cycloaddition. [Ir(cod)Cl]2/DPPE also catalyzed the cycloaddition of α,ω-diynes with 2,5-dihydrofuran to give bicyclic cyclohexadiene derivatives. The reaction with 2,3-dihydrofuran and n-butyl vinyl ether gave benzene derivatives instead of cyclohexadiene derivatives. We also propose a mechanism to account for this novel aromatization that includes cleavage of the C-O bond.
- Kezuka, Satoko,Tanaka, Shigeru,Ohe, Toshihito,Nakaya, Yoshihiko,Takeuchi, Ryo
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- Energetic interpenetrating polymer network based on orthogonal azido-alkyne click and polyurethane for potential solid propellant
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High energetic propellants with synergistic mechanical strength are the prerequisites for aerospace industry and missile technology; though glycidyl azide polymer (GAP) is a renowned and a promising energetic polymer which shows poor mechanical and low-temperature properties. In order to overcome these problems, a novel energetic interpenetrating polymer network (IPN) of acyl-terminated glycidyl azide polymer (Acyl-GAP) and hydroxyl terminated polybutadiene (HTPB) is effectively synthesized and characterized via an "in situ" polymerization by triazole and urethane curing system respectively. Acyl-GAP and dimethyl 2,2-di(prop-2-ynyl)malonate (DDPM) have been synthesized and well characterized by using FT-IR, 1H NMR, 13C NMR and GPC. The maximum tensile strength ~5.26 MPa and elongation 318% are achieved with HTPB-PU/Acyl-GAP triazole in 50 : 50 weight ratios. The solvent resistance properties have been investigated by the equilibrium swelling method and the glass transition temperature (Tg), morphology and thermal stability are evaluated by DSC, SEM and TGA-DTG respectively. Thus, HTPB-PU/Acyl-GAP triazole is a futuristic binder for the composite solid propellant.
- Tanver, Abbas,Huang, Mu-Hua,Luo, Yunjun,Khalid, Syed,Hussain, Tariq
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- Nbcl5/zN/PCy3-system-catalyzed intramolecular [2 + 2 + 2] cycloadditions of diynes and alkenes to form bicyclic cyclohexadienes
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A NbCl5, Zn, and PCy3 catalytic system that generated low-valent Nb species is used for the synthesis of bicyclic cyclohexadienes from diynes and simple alkenes. A phosphine ligand is important for stabilizing low-valent Nb in the cycloaddition. The bicyclic cyclohexadiene skeleton is important in transition-metal-catalyzed intramolecular cycloadditions.
- Watanabe, Keisuke,Satoh, Yasushi,Kamei, Motofumi,Furukawa, Hirohisa,Fuji, Maito,Obora, Yasushi
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- Synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids
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Unique chiral spiro ionic liquids based on 1,2,3-triazolium salts were synthesized via an intramolecular double Huisgen reaction. The optical resolution of the liquid precursors and subsequent dialkylations leads to chiral spiro triazolium salts on a gram
- Yoshida, Yasushi,Takizawa, Shinobu,Sasai, Hiroaki
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- Cyclopolymerization of dimethyl dipropargylmalonate in supercritical carbon dioxide to give a highly regular polyene containing predominantly five-membered rings
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Poly(dimethyl dipropargylmalonate) synthesized in scCO2 contained more than 95% five-membered rings, i.e., highly regular polyene was produced, which shows carbon dioxide as a reaction medium plays a significant role in determining a highly selective polymer structure. The Royal Society of Chemistry 2005.
- Pack, Ji Won,Hur, Young-Jae,Kim, Hwayong,Lee, Youn-Woo
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- First examples of cobalt-mediated formal Alder ene reaction of allenynes
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CpCo(CO)2 catalyzes the Alder ene reaction of allenynes 1 to afford six-membered carbocycles in a totally regioselective manner through, presumably, η3-allyl hydride complexes mechanism.
- Llerena, Dominique,Aubert, Corinne,Malacria, Max
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- Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels-Alder (HDDA) Derived Benzynes with Oxazoles
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A capture reaction of hexadehydro-Diels-Alder (HDDA) derived benzyne with various substituted oxazoles is reported. With methyl, hydrogen, or phenyl as the substituent at 2-position of oxazole, tetraynes afforded epoxyanthracene derivatives or underwent dicarbonylation on benzene ring. The reaction does not require any catalyst or additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compared with traditional benzyne.
- Yang, Feihu,Zheng, Xiaojie,Lei, Yu,Hu, Qiong,Zhu, Wenjing,Hu, Yimin
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supporting information
p. 1125 - 1133
(2021/11/22)
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- SPIROCYCLIC ANDROGEN RECEPTOR PROTEIN DEGRADERS
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The present disclosure provides compounds represented by Formula( I ) and the salts or solvates thereof, wherein R3a, E, L, A1, B1, X1, X2, Z1, and Z2 are as defined in the specification. Compounds having Formula (I) are androgen receptor degraders useful for the treatment of cancer and other diseases.
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Paragraph 01165-01166
(2021/04/01)
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- Synthesis of [6,6,m]-Tricyclic Compounds via [4+2] Cycloaddition with Au or Cu Catalyst
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We synthesized [6,6,6]- and [6,6,7]-tricyclic compounds via intramolecular [4+2] cycloaddition by gold or copper catalysts. Substrates for cyclization were prepared by coupling reactions between eight types of diyne and four types of aromatic moieties. We have successfully synthesized eleven tricyclic compounds.
- Kang, Juyeon,Ham, Seunghwan,Seong, Chaehyeon,Oh, Chang Ho
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supporting information
p. 1039 - 1043
(2021/05/05)
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- Synthesis and Characterization of Bis-1,2,3-Triazole Ligand and its Corresponding Copper Complex for the Development of Electrochemical Affinity Biosensors
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The bis-triazole ligand and its corresponding copper complexes were synthesized and characterized for the first time and proposed as new labels for the development of electrochemical aptasensors. The bis-triazole ligand was prepared from methyl 1,6-heptad
- Ben Jrad, Amani,Calas-Blanchard, Carole,Inguimbert, Nicolas,Kanso, Hussein,Noguer, Thierry,Philouze, Christian,Rammal, Wassim,Thomas, Fabrice
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p. 9580 - 9588
(2021/05/27)
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- Fully Substituted Conjugate Benzofuran Core: Multiyne Cascade Coupling and Oxidation of Cyclopropenone
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An unprecedented C═C double bond cleavage of cyclopropenone and dioxygen activation by multiyne cascade coupling has been developed. This chemistry provides a novel, simple, and efficient approach to synthesize fully substituted conjugate benzofuran derivatives from simple substrates under mild conditions. The density functional theory (DFT) calculations reveal that the unique homolytic cleavages of cyclopropenone and molecular oxygen are crucial to the success of this reaction.
- Yao, Liangliang,Hu, Qiong,Bao, Li,Zhu, Wenjing,Hu, Yimin
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supporting information
p. 4971 - 4975
(2021/06/30)
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- Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2?+?2?+?2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi
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Rhodium-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulations and nitroalkene reactions have been employed for the synthesis of 56 quinone-based compounds. These were evaluated against Trypanosoma cruzi, the parasite that causes Chagas disease. The reactions described here are part of a program that aims to utilize modern, versatile and efficient synthetic methods for the one or two step preparation of trypanocidal compounds. We have identified 9 compounds with potent activity against the parasite; 3 of these were 30-fold more potent than benznidazole (Bz), a drug used for the treatment of Chagas disease. This article provides a comprehensive outline of reactions involving over 120 compounds aimed at the discovery of new quinone-based frameworks with activity against T. cruzi.
- Wood, James M.,Satam, Nishikant S.,Almeida, Renata G.,Cristani, Vinicius S.,de Lima, Dênis P.,Dantas-Pereira, Luiza,Salom?o, Kelly,Menna-Barreto, Rubem F.S.,Namboothiri, Irishi N.N.,Bower, John F.,da Silva Júnior, Eufranio N.
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- Access to Benzoxazepines and Fully Substituted Indoles via HDDA Coupling
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The HDDA-derived benzyne intermediate was captured by oxazolines based on the addition reaction of benzyne to the Ca?N double bond. Benzoxazepine derivatives, fused benzoxazepine derivatives, and fully substituted indoles are synthesized in one step. The reaction does not require any catalyst or additives. Possible reaction mechanisms are presented.
- Zheng, Xiaojie,Liu, Baohua,Yang, Feihu,Hu, Qiong,Yao, Liangliang,Hu, Yimin
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supporting information
p. 956 - 959
(2020/02/15)
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- Polysubstituted dibenzoylbenzene derivative and synthesis method thereof
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The invention provides a polysubstituted dibenzoylbenzene derivative and a synthesis method thereof. The synthesis method comprises the following steps: tetraacetylene and 2,4-diphenyl oxazole are subjected to a DA reaction in methylbenzene under a heating condition, and the system is naturally cooled to room temperature in order to stop the reaction; and the product is purified and separated to obtain the polysubstituted dibenzoylbenzene derivative. Compared with existing polysubstituted dibenzoylbenzene, the polysubstituted dibenzoylbenzene derivative belongs to a series of novel polysubstituted dibenzoylbenzene derivatives. The prepared polysubstituted dibenzoylbenzene has a more complex and diverse structure than common polysubstituted dibenzoylbenzene. The polysubstituted dibenzoylbenzene derivative can be widely applied to the pharmaceutical industry, and the preparation method has the advantages of simplicity, high efficiency and short reaction time.
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Paragraph 0040; 0043; 0046-0047
(2020/02/19)
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- Phenanthrenes/dihydrophenanthrenes: The selectivity controlled by different benzynes and allenes
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A method for the intermolecular annulation of benzynes with allenes is disclosed. This protocol utilized allenes as an unconventional diene component for the selective synthesis of phenanthrenes and dihydrophenanthrenes under the control of different benzyne precursors, featuring high atom-economy and good functional group compatibility. Density functional theory (DFT) calculations reveal that different migratory routes of the aromatic C-H bond are crucial for the observed selectivity. This journal is
- Yao, Liangliang,Fang, Bo,Hu, Qiong,Lei, Yu,Bao, Li,Hu, Yimin
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supporting information
p. 15185 - 15188
(2020/12/21)
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- Au-Cavitand Catalyzed Alkyne-Acid Cyclizations
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Supramolecular cavitands that contain inwardly directed functional groups have yielded specialized transformations and trapping of reactive intermediates. A recently reported 3-wall Au cavitand provides exciting opportunities for supramolecular catalysis. In this study, a variety of substituted γ-alkynoic acids were reacted to give lactones. The interaction of peripheral “R” groups revealed differential catalyst behavior. Extremely large and small groups reacted with appreciable rate. Intermediate sized groups however, slowed significantly: giving support that size-specific binding is at play when using cavitands as a scaffold for gold catalysis. These results serve as some of the first evidence of the interplay between substrate and cavitand interior in the catalytic sphere.
- Ho, Tam D.,Schramm, Michael P.
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supporting information
p. 5678 - 5684
(2019/08/21)
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- A multi-substituted indole derivative and its preparation method (by machine translation)
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The invention provides a multi-substituted indole derivative and its preparation method, is in the absence of catalyst, additive-free, non-protective state, using toluene as a solvent, in the 100 - 110 °C by four alkyne substrate with 2, 4 - diphenyl - 4,
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Paragraph 0042; 0046
(2019/03/08)
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- The exocyclic double bond of a nitrogen-containing heterocyclic derivatives and its preparation method (by machine translation)
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The invention provides a of the exocyclic double bond oxygen and nitrogen heterocyclic derivatives and its preparation method, the preparation method is: the four-alkyne apperception compound in toluene solvent with 2, 4, 4 - trimethyl - 2 - oxazoline heating reaction, after the reaction, natural cooling to room temperature, the product purification and separation, by the outer double bond containing an oxygen and nitrogen heterocyclic derivatives. Compared with the prior art, the present invention provides a series of new containing an outer double bond of the oxygen and nitrogen heterocyclic derivatives of the preparation method. As to the ordinary heterocyclic derivatives, the preparation of the invention containing an outer double bond of nitrogen heterocyclic derivatives have the exocyclic double bond and the existence of effinity atoms, and get the rare of the seven-membered ring structure, its structure is more complex and novel. The invention material may be in the in medical industry also can have a broader role, and the present invention provides a preparation method, high-efficiency, short reaction time, efficiency is high. (by machine translation)
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Paragraph 0054; 0057; 0058
(2019/06/30)
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- COMPOUNDS AND DEVICES CONTAINING SUCH COMPOUNDS
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Disclosed herein are novel compounds. Such compounds may be synthesized using a hexadehydro-Diels- Alder (HDD A) reaction. Also disclosed are organic devices including one or more disclosed compounds. The organic devices can include organic electronic devices, organic photonic devices, or combinations thereof. Specific types of devices can include, for example, organic light-emitting diodes (OLEDs), organic photovoltaic (OPV) devices, organic field-effect transistors (OFETs), or combinations thereof.
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Page/Page column 77
(2018/03/25)
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- Palladium-catalyzed silaborative carbocyclizations of 1,6-diynes
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An addition/cyclization reaction of 1,6-diynes was developed for the synthesis of highly substituted 1,2-dialkylidenecycloalkanes. In this work, 1,6-diynes reacted with (dimethylphenylsilyl)pinacol-borane in the presence of a palladium catalyst to afford 1,2-dialkylidenecycloalkanes bearing silyl and boryl groups with a (Z,Z)-configuration in good to excellent yields. Moreover, the corresponding products could be easily converted into other synthetically useful compounds. This protocol provides an efficient and practical method of heteroelement-element linkage addition to the unsaturated 1,6-diynes.
- Zhang, Qian,Liang, Qiu-Ju,Xu, Jian-Lin,Xu, Yun-He,Loh, Teck-Peng
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supporting information
p. 2357 - 2360
(2018/03/13)
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- Polysubstituted acrylate derivatives and preparation method thereof
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The invention provides polysubstituted acrylate derivatives and a preparation method thereof. Compared with existing acrylate derivatives, a series of novel acrylate derivatives are provided. Comparedwith common acrylate derivatives, the prepared acrylate derivatives have multiple rings and more complex and diversified structures. The substances can be widely applied to the medicine industry, andthe provided preparation method is convenient, efficient, short in reaction time and high in efficiency.
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Paragraph 0071
(2018/05/16)
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- Dodecahydrobenzodiindanophenanthrene derivatives and synthesis method thereof
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The invention discloses dodecahydrobenzodiindanophenanthrene derivatives and a synthesis method thereof. Compared with the prior art, the invention provides a series of novel benzodiindanophenanthrenederivatives. Compared with the ordinary benzodiindanophenanthrene derivative, the benzodiindanophenanthrene derivatives prepared by the synthesis method provided by the invention have the advantagesas follows: due to existence of multiple rings, the benzodiindanophenanthrene derivatives are more complex and diverse in structure; the benzodiindanophenanthrene derivatives can be prepared into a variety of medicines, can be applied to synthetic resin, plant growth hormones, vat dyes, tanning materials and the like, and also show a brighter application prospect in chemical production; in addition, a preparation method provided by the invention is simple, convenient, short in reaction time and high in efficiency.
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Paragraph 0038; 0045
(2018/05/16)
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- Oxazinyl phenyl ether derivative and preparation method thereof
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The invention provides an oxazinyl phenyl ether derivative and a preparation method thereof. Butyne reacts with 2-phenyl-3,4-diydro-2H-benzo[1,3]oxazin-4-one at 110-115 DEG C in toluene used a solventin a catalyst-free and additive-free unprotected state for 15 h or more, the reaction process firstly comprises self-cyclization of the butyne substrate, and benzyne formed by the butyne is an electron-deficient intermediate, and is extremely unstable and highly active. The preparation method comprises the following steps: carrying out an HDDA reaction on the butyne to form the benzyne intermediate, and carrying out nucleophilic addition on the highly active benzyne intermediate and 2-phenyl-3,4-diydro-2H-benzo[1,3]oxazin-4-one to obtain the oxazinyl phenyl ether derivative. The oxazinyl phenyl ether derivative prepared in the invention has a polycyclic structure, and has complex and diverse structures; and compared with the prior art, the preparation method has the advantages of simplicity, short reaction time and high efficiency.
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Paragraph 0043-0044
(2018/12/02)
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- Ferrocene derivative and preparation method thereof
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The invention provides a ferrocene derivative and a preparation method thereof. Compared with the prior art, in the absence of catalyst and additive as well as protection and with toluene as a solvent, a tetra-alkyne substrate reacts with ferrocene at 104-114 DEG C, wherein the reaction process comprises the following steps: cyclization of the tetra-alkyne substrate, generation of a benzyne intermediate through a HDDA reaction, and 4+2 cycloaddition reaction between the highly active benzyne intermediate and the cyclopentadiene of ferrocene to obtain the ferrocene derivative. The method breaksthrough the former knowledge that the ferrocene cannot experience a cycloaddition reaction, and also shows a broader application prospect in chemical production and clinical medicine. Moreover, the preparation method provided by the invention has the advantages of simplicity and convenience, high efficiency and short reaction time.
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Paragraph 0050; 0051
(2018/12/02)
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- Copper-Mediated Nucleophilic Addition/Cascade Cyclization of Aryl Diynes
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Treatment of diyne substrates with sulfinate salts under the action of copper(II) triflate results in a cascade cyclization reaction. The reaction involves nucleophilic addition of the sulfinate and formation of two new C-C bonds with concomitant cleavage of an aryl C-H bond. The reaction proceeds in good yields with a range of diyne precursors and sulfinate salts. Preliminary mechanistic analysis reveals a rare example of an operative ionic mechanism in contrast to other related cyclizations.
- Sinclair, Geoffrey S.,Yang, Tianyu,Wang, Sunmeng,Chen, Wei H.,Schipper, Derek J.
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supporting information
p. 802 - 805
(2017/03/01)
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- Photochemical Hexadehydro-Diels-Alder Reaction
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We demonstrate that the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction to produce reactive benzyne derivatives can be initiated photochemically. As with the thermal variant of the HDDA process, the reactive intermediates are formed in the absence of reagents or the resulting byproducts required for the generation of benzynes by traditional methods. This photo-HDDA (or hν-HDDA) reaction occurs at much lower temperatures (including even at -70 °C) than the thermal HDDA, but the benzynes produced behave in the same fashion with respect to their trapping reactions, suggesting they are of the same electronic state.
- Xu, Feng,Xiao, Xiao,Hoye, Thomas R.
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supporting information
p. 8400 - 8403
(2017/07/06)
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- A cinnamic acid ester derivative and its preparation method (by machine translation)
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The invention relates to a cinnamic acid ester derivative and its preparation method. Cinnamic acid ester derivatives of structural formula is: the preparation method includes in the sodium hydride under the catalysis, will be a two-ester and proparagyl bromide in anhydrous acetonitrile reaction to obtain white solid product; white solid product with the phenylacetylene bromide or substituted phenylacetylene bromide in Pd (PPh3 )2 Cl2 Under the catalysis of the/CuI, to triethylamine makes the alkali, in anhydrous second grade nitrile in brown color solid product obtained; in the 90 - 110 °C under the condition of, the light brown solid product in toluene in between with the bromo cinnamic acid to obtain the cinnamic acid ester derivatives. The present invention provides generating a series of new cinnamic acid ester derivatives. As to the ordinary cinnamic acid ester derivative, this invention preparation of cinnamic acid ester derivative is the existence of multi-ring, its structure is more complex and diverse, in chemical production, in clinical medicine also will show more extensive use prospect. (by machine translation)
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Paragraph 0043; 0046-0048
(2017/08/02)
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- One-step constructed C-O and C-S bond bifunctional product and preparation method thereof
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The invention provides a one-step constructed C-O and C-S bond bifunctional product and a preparation method thereof. Compared with the prior art, the invention provides a series of novel C-O and C-S bond bifunctional products and derivatives thereof. The C-O and C-S bond bifunctional products and the derivatives thereof are constructed with a one-step method through a cascade reaction of different alkyne substrates; the reaction overcomes the defects that transition metal needs to be added for catalysis, requirements for substrates and reaction conditions are harsh and the like, reagents for the reaction are lower in price, target molecules are obtained with a high-atom-economy and environment-friendly method and a new and more practical method is provided for efficient construction of carbon-heteroatomic bonds.
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Paragraph 0040; 0041; 0042; 0043; 0044
(2017/07/20)
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- Polysubstituted condensed aromatic derivatives, and preparation method thereof
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The invention discloses polysubstituted condensed aromatic derivatives, and a preparation method thereof. Compared with the prior art, the preparation method comprises following advantages: witting reagent is adopted, electron transfer reaction is carried out, no catalyst is used, high efficiency synthesis of the polysubstituted condensed aromatic derivatives is realized under simple conditions, reaction time is short, efficiency is high, and a series of novel polysubstituted condensed aromatic derivatives are provided. Compared with common polysubstituted condensed aromatic derivatives, the structures are more complex and diverse; and application prospect in the field of chemical production and clinical medical industry is more promising.
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Paragraph 0038; 0042
(2017/10/12)
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- A multi-substituted 3 - phenyl phenol derivatives and its preparation method (by machine translation)
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The invention provides a multi-substituted 3 - phenyl phenol derivatives and its preparation method, compared with the prior art, the present invention provides a series of new multi-substituted 3 - phenyl phenol derivatives. As to the ordinary multi-substituted 3 - phenyl phenol derivatives, the invention preparation of multiple-substituted 3 - phenyl phenol derivatives is the existence of multi-ring, its structure is more complex and diverse, in chemical production, clinical medicine, material also will show more extensive use prospect. And, the present invention provides a preparation method, high-efficiency, short reaction time, efficiency is high. (by machine translation)
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Paragraph 0037; 0038
(2017/08/29)
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- Poly-substituted condensed benzofuran derivatives and preparation method thereof
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The invention provides poly-substituted condensed benzofuran derivatives and a preparation method thereof. Compared with the prior art, a series of poly-substituted condensed benzofuran derivatives is provided. Compare with common poly-substituted condensed benzofuran derivatives, the prepared poly-substituted condensed benzofuran derivatives have a multi-ring structure, the structure is more complicated, and thus the provided derivatives have a wide application in industries such as chemical engineering, clinical medicine, materials, and the like. Furthermore, the provided preparation method has the advantages of simpleness, high efficiency, and short reaction time.
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Paragraph 0043
(2017/08/29)
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- Poly-substituted condensed aromatic derivative and preparation method thereof
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The invention provides a poly-substituted condensed aromatic derivative and a preparation method thereof. Compared with the prior art, in the preparation method, the poly-substituted condensed aromatic derivative is simply, conveniently and efficiently synthesized under the catalyst-free condition by utilizing transfer of witting reagent related electrons and other reaction processes from a new perspective, the reaction time is short, and the efficiency is high. In addition, a series of novel poly-substituted condensed aromatic derivatives are provided. Compared with common poly-substituted condensed aromatic derivatives, the poly-substituted condensed aromatic derivative is complicate and diversified in structure and also has wide application prospect in chemical production and clinic medicine.
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Paragraph 0036
(2017/08/28)
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- Dibenzothiophene compound and preparation method thereof
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The invention provides a dibenzothiophene compound and a preparation method thereof. Compared with the prior art, the invention provides a brand new method for compounding the dibenzothiophene compound under inexistence of metal catalysis, for generating a series of new dibenzothiophene compounds. The compounded dibenzothiophene compound has more complex and various structures and has excellent application at the aspects of medicines, dyestuff, biology, and the like.
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Paragraph 0046; 0047
(2018/01/17)
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- Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels-Alder Cascade Reaction
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We describe here three alkynyl substituted naphthalenes that display promising luminescence characteristics. Each compound is easily and efficiently synthesized in three steps by capitalizing on the hexadehydro-Diels-Alder (HDDA) cycloisomerization reacti
- Xu, Feng,Hershey, Kyle W.,Holmes, Russell J.,Hoye, Thomas R.
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supporting information
p. 12739 - 12742
(2016/10/13)
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- Reactions of HDDA-Derived Benzynes with Perylenes: Rapid Construction of Polycyclic Aromatic Compounds
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Benzynes produced by the thermal cycloisomerization of tetrayne substrates [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with perylenes to produce novel naphthoperylene derivatives. Cyclic voltammetry and absorption and emission properties of these compounds are described. DFT studies shed additional light on the dearomatization that accompanies the reaction as well as some of the spectroscopic behavior.
- Xu, Feng,Xiao, Xiao,Hoye, Thomas R.
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supporting information
p. 5636 - 5639
(2016/11/17)
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- A Ruthenium Complex-Catalyzed Cyclotrimerization of Halodiynes with Nitriles. Synthesis of 2- and 3-Halopyridines
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Monohalo- and dihalodiynes efficiently undergo [2+2+2] cyclotrimerization with nitriles in the presence of a catalytic amount of the ruthenium complex Cp*RuCl(cod) (10 mol%) to afford the corresponding halopyridines under ambient conditions in good isolated yields (up to 90%). The halopyridines are formed as two separable regioisomers. This is the first example of a direct synthesis of halopyridines from haloalkynes and nitriles. (Figure presented.) .
- Bedná?ová, Eva,Colacino, Evelina,Lamaty, Frédéric,Kotora, Martin
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supporting information
p. 1916 - 1923
(2016/07/06)
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- A New Approach for the Synthesis of Highly Substituted Aromatic Rings: The Alkyne-Mediated Approach
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Pentasubstituted aromatic rings serve as templates for drug design and can be conveniently prepared by the thermolysis of suitably substituted alkynes under microwave conditions. Rings in the microwave! Pentasubstituted aromatic rings serve as templates for drug design and can be conveniently prepared by the thermolysis of suitably substituted alkynes under microwave conditions.
- Parsons, Philip J.,Jones, Daniel R.,Padgham, Alex C.,Allen, Lewis A. T.,Penkett, Clive S.,Green, Robert A.,White, Andrew J. P.
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supporting information
p. 3981 - 3984
(2016/03/16)
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- A salicyldehyde derivative and its preparation method (by machine translation)
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The present invention provides salicylaldehyde derivatives and a preparation method thereof. The preparation method comprises: a, precursor synthesis; b, target product synthesis; and c, purification. Compared with the salicylaldehyde derivative and the preparation method thereof in the prior art, the salicylaldehyde derivative and the preparation method thereof of the present invention have the following characteristics that: the completely-new poly-substituted salicylaldehyde derivative synthesis method is provided, a series of the new salicylaldehyde derivatives are produced, and compared with the ordinary salicylaldehyde derivative, the prepared salicylaldehyde derivative of the present invention has multiple rings so as to have the complex and diverse structure, and presents wide application prospects in chemical engineering production and clinical medicine.
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Paragraph 0063; 0065
(2016/10/08)
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- Fused naphthalene nucleus compounds and preparation method thereof
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The invention discloses fused naphthalene nucleus compounds and a preparation method thereof. Compared with the prior art, the invention provides a brand-new synthetic method for multi-substituted naphthalene derivatives to generate a series of new naphthalene derivatives. Compared with other naphthalene derivatives, the naphthalene derivatives prepared by the invention comprise more nucleuses, are more complex and diverse in structure, and show wider application and prospects in chemical production and clinical medicine.
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Paragraph 0050; 0051
(2016/10/10)
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- Oxidation reduction method of tetrayne compound and diphenylthiocarbazone
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The invention discloses an oxidation reduction method of a tetrayne compound and diphenylthiocarbazone. Compared with the prior art, the brand new oxidation reduction method of the tetrayne compound and diphenylthiocarbazone has the advantages as follows: new oxidation reduction products are produced, and the oxidation reduction method has the broad application prospect; besides, the oxidation reduction method is simple to operate, high in reaction efficiency and mild in reaction condition.
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Paragraph 0023
(2016/10/10)
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- A b benzocarbazoles selenol derivative and its preparation method (by machine translation)
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The invention provides a two benzocarbazoles selenol derivative and its preparation method, the preparation method comprises the following steps: using sodium hydride as catalyst, will be added to the propargyl bromide that is commercialized with malonic
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Paragraph 0057; 0058
(2016/10/31)
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- Benzodihydropyran ring derivative and preparation method thereof
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The invention discloses a benzodihydropyran ring derivative and a preparation method thereof. The malonate and propargyl bromide are used as initial raw materials to synthesize a benzodihydropyran ring derivative through a three-step reaction; and the raw material is simple and easy to obtain, the synthesis method is convenient and fast, and an efficient and fast synthesis path is provided for the preparation of the benzodihydropyran ring derivative.
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Paragraph 0046; 0049; 0050; 0051
(2016/11/24)
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- An ortho-mercat phenol derivative and its preparation method (by machine translation)
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This invention has offered a kind of ortho-mercat phenol derivative and its preparation method, the preparation method comprises: a, precursor synthesis; b, the target product synthesis; c, purified. Compared with the prior art, the present invention, provides a new multi-substituted ortho-mercat phenolic synthetic method, generating a new series of ortho-mercat phenol derivatives. As to the ordinary ortho-mercat phenol derivatives, the present invention provides method for preparing ortho-mercat phenol derivatives of the existence of a plurality of ring, its structure is more complex and varied, in chemical production, in clinical medicine will also demonstrate the use of more extensive prospect. (by machine translation)
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Paragraph 0066
(2017/02/24)
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- Visible Light-Gated Cobalt Catalysis for a Spatially and Temporally Resolved [2+2+2] Cycloaddition
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The ability to exert spatial and temporal control over a transition-metal catalyst offers diverse opportunities for the fabrication of functional materials. Using an external stimulus such as visible light to toggle a catalyst between an active and dorman
- Ruhl, Kyle E.,Rovis, Tomislav
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supporting information
p. 15527 - 15530
(2016/12/16)
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- A tetrazole heterocyclic compound and its preparation method
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The invention provides a tetrazole heterocyclic compound and a preparation method thereof. The preparation method comprises the steps of adding dimethyl malonate and propargyl bromide into anhydrous acetonitrile to react in the presence of sodium hydride serving as a catalyst;; mixing the obtained product and phenylethynyl bromide in a water-free and oxygen-free catalyzing system of Pd(PPh3)2Cl2/CuI; agitating to react under room temperature by using triethylamine serving as alkali and anhydrous acetonitrile as a solvent so as to obtain another product; enabling the product to react with 2-bromine phenyl tetrazole in a m-bromotoluene solvent to obtain the tetrazole heterocyclic compound. Compared with the common tetrazole compound, the tetrazole heterocyclic compound prepared by the method contains multiple rings and accordingly has the advantage that the structure is complex and diverse; therefore, the tetrazole heterocyclic compound has a good application prospect in the chemical production and clinical medicines.
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Paragraph 0024; 0026
(2017/03/08)
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- Base-induced cyclization of derivatives of bispropargylated acetic acid to m -toluic acid
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A base-induced cyclization reaction of 1,1-bispropargyls has been examined. Alkali treatment of 2,2-bispropynyl acetic acid derivatives in aqueous ethanol mostly provided 3-methylbenzoic acid. Investigations on substituent effects indicate the requirement of an electron-withdrawing group causing CH acidity and the center of the dipropargylic structure. Besides, an intramolecular hydrogen transfer causing the rearrangement of one terminal alkyne into a corresponding allene appears to be essential. Despite an unsatisfying conversion yield of below 40%, the reaction is interesting due to the mild cyclization conditions.
- Ali, Tammar Hussein,Heidelberg, Thorsten,Hussen, Rusnah Syahila Duali
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supporting information
p. 1361 - 1364
(2015/06/16)
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- Iron(ii)-catalysed [2+2+2] cycloaddition for pyridine ring construction
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We report a new, simple and air-stable iron(ii) complex pre-catalyst for the synthesis of substituted pyridines via a [2+2+2] cycloaddition between diynes and nitrile derivatives. The Royal Society of Chemistry 2014.
- Richard, Vincent,Ipouck, Melinda,Merel, Delphine S.,Gaillard, Sylvain,Whitby, Richard J.,Witulski, Bernhard,Renaud, Jean-Luc
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supporting information
p. 593 - 595
(2014/01/06)
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- Synthesis of substituted [8]cycloparaphenylenes by [2 + 2 + 2] cycloaddition
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A new modular approach to the smallest substituted cycloparaphenylenes (CPPs) is presented. This versatile method permits access to substituted CPPs, choosing the substituent at a late stage of the synthesis. Variously substituted [8]CPPs have been synthesized, and their properties analyzed. The structural characteristics of substituted CPPs are close to those of unsubstituted CPPs. However, their optoelectronic behavior differs remarkably due to the larger torsion angle between the phenyl units.
- Tran-Van, Anne-Florence,Huxol, Elena,Basler, Jonathan M.,Neuburger, Markus,Adjizian, Jean-Joseph,Ewels, Chris P.,Wegner, Hermann A.
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supporting information
p. 1594 - 1597
(2014/04/17)
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- A strain induced change of mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] cycloaddition reaction
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While investigating the [2 + 2 + 2] cycloaddition as a tool to build up strained oligophenyl systems with a diyne-ethylene glycol macrocyle, a surprising change of mechanism was observed. Instead of the expected [2 + 2 + 2] para-terphenyl, the ortho-terphenyl product explained by a formal [2 + 1 + 2 + 1] cycloaddition was formed. An η4-coordinated metal-cyclobutadiene is proposed as the key structure in the catalytic cycle, which is formed to release the induced strain. The optical properties of the ortho-terphenyl products have been measured as well as the coordination ability of Na+ and K+.
- Tran-Van, Anne-Florence,Goetz, Silas,Neuburger, Markus,Wegner, Hermann A.
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supporting information
p. 2410 - 2413
(2014/05/20)
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- Phosphine-promoted cyclization of dicyclopropenones
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A novel phosphine-promoted intramolecular cyclization of dicyclopropenones 1 has been described in this contribution. A variety of 2,3-dihydro-1H-indene-4, 6-diol derivatives 2 and hexahydropentalen-2-one derivatives 3 were obtained selectively in moderat
- Yang, Jin-Ming,Tang, Xiang-Ying,Wei, Yin,Shi, Min
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supporting information
p. 3545 - 3552
(2014/01/06)
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- Enantioselective, desymmetrizing bromolactonization of alkynes
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Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD) 2PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter, are valuable building blocks for synthetic chemistry.
- Wilking, Michael,Mueck-Lichtenfeld, Christian,Daniliuc, Constantin G.,Hennecke, Ulrich
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supporting information
p. 8133 - 8136
(2013/07/05)
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- Pd(ii)-SDP-catalyzed enantioselective 5-exo-dig cyclization of γ-alkynoic acids: Application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center
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The Pd(ii)-SDP-catalyzed first enantioselective intramolecular cyclization of α,α-disubstituted γ-alkynoic acids is described. This 5-exo-dig cyclization afforded dihydrofuran-2(3H)-ones bearing a chiral quaternary carbon center in excellent yields with e
- Sridharan, Vellaisamy,Fan, Lulu,Takizawa, Shinobu,Suzuki, Takeyuki,Sasai, Hiroaki
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supporting information
p. 5936 - 5943
(2013/09/12)
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