- A Domino Heck Coupling-Cyclization-Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines
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An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.
- Ghora, Santanu,Sreenivasulu, Chinnabattigalla,Satyanarayana, Gedu
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p. 393 - 402
(2021/10/21)
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- SmI2-mediated C-alkylation of Ketones with Alcohols under Microwave Conditions: A Novel Route to Alkylated Ketones
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A novel protocol is developed towards the preparation of alkylated ketones from alcohols in presence of catalytic amount of SmI2 and base with the elimination of water as a single by-product under microwave irradiation conditions. Furthermore, applicability of this methodology to the synthesis of Donepezil and late-stage functionalization in Pregnenolone is also reported. Successful application of this methodology in Friedl?nder quinolone synthesis using 2-aminobenzyl alcohol and various acetophenones expand the synthetic utility of this protocol.
- Gour, Jitendra,Kar, Swayamsiddha,Mahammad Ghouse, Shaik,Manohar Chelli, Sai,Nanduri, Srinivas,Pawar, Gaurav,Reddy Dannarm, Srinivas,Sonti, Rajesh
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- NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
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Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.
- Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin
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p. 7772 - 7779
(2021/06/30)
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- Asymmetric Synthesis of Hydroquinolines with α,α-Disubstitution through Organocatalyzed Kinetic Resolution
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The first kinetic resolution of hydroquinoline derivatives with α,α-disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate- and enantio-determining electrophilic attack promoted by a network of attractive non-covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N-heterocycles with α,α-disubstitution.
- Chen, Yunrong,Zhu, Chaofan,Guo, Zheng,Liu, Wei,Yang, Xiaoyu
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supporting information
p. 5268 - 5272
(2021/02/05)
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- Kinetic Resolution of 2,2-Disubstituted Dihydroquinolines through Chiral Phosphoric Acid-Catalyzed C6-Selective Asymmetric Halogenations
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A novel kinetic resolution of 2,2-disubstituted dihydroquinolines was achieved by regioselective asymmetric halogenations enabled by chiral phosphoric acid catalysis. A series of dihydroquinolines bearing 2,2-disubstitutions were well-tolerated in these reactions, generating both the recovered dihydroquinolines and C-6-brominated products with high enantioselectivities, with s-factors up to 149. In addition, this kinetic resolution protocol is also applicable for 2,2-disubstituted tetrahydroquinoline and asymmetric iodonation reaction.
- Chen, Yunrong,He, Yu-Peng,Liu, Wei,Tao, Houchao,Yang, Xiaoyu,Zhao, Fei,Zhu, Chaofan
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supporting information
p. 4104 - 4108
(2021/06/27)
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- Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt
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A ruthenium complex bearing a functional 2,2′-bibenzimidazole ligand [(p-cymene)Ru(BiBzImH2)Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically active molecular was also undertaken. Notably, this research exhibits new potential of metal–ligand bifuctional catalysts for acceptorless dehydrogenative reactions.
- Xu, Xiangchao,Ai, Yao,Wang, Rongzhou,Liu, Liping,Yang, Jiazhi,Li, Feng
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p. 340 - 349
(2021/02/27)
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- Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst
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This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.
- Xu, Jing-Xiu,Pan, Nan-Lian,Chen, Jia-Xi,Zhao, Jin-Wu
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p. 10747 - 10754
(2021/08/16)
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- Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N -Iodosuccinimide
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Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N -iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N -iodosuccinimide.
- Naruto, Hiroki,Togo, Hideo
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p. 1122 - 1130
(2020/04/01)
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- Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process
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A continuous photochemical process is presented that renders a series of quinoline products via an alkene isomerization and cyclocondensation cascade. It is demonstrated that a high-power LED lamp generates the desired targets with higher productivity and efficiency than a medium-pressure Hg-lamp. The scope of this tandem process is established and allows for the generation of various substituted quinolines in high yields and with throughputs of greater than one gram per hour. Finally, this effective flow process is coupled with a telescoped hydrogenation reaction to render a series of tetrahydroquinolines including the antimalarial natural product galipinine.
- Di Filippo, Mara,Baumann, Marcus
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p. 6199 - 6211
(2020/08/26)
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- A nanoscale iron catalyst for heterogeneous direct: N - And C -alkylations of anilines and ketones using alcohols under hydrogen autotransfer conditions
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Here, we report a commercially available nanoscale Fe catalyst for heterogeneous direct N- and C-alkylation reactions of anilines and methyl ketones with alcohols. A hydrogen autotransfer mechanism has been found to operate in these reactions by deuterium labelling studies. In addition, dehydrogenative quinoline synthesis has been demonstrated from amino benzyl alcohols and acetophenones.
- Nallagangula, Madhu,Sujatha, Chandragiri,Bhat, Venugopal T.,Namitharan, Kayambu
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supporting information
p. 8490 - 8493
(2019/07/22)
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- An Efficient Mesoporous Cu-Organic Nanorod for Friedl?nder Synthesis of Quinoline and Click Reactions
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Within the green chemistry context, heterogeneous catalysis for the synthesis of N-heterocycles from renewable resources using non-precious metals has garnered great interest in terms of economic and environmental perspectives. Herein, we present a triazine functional hierarchical mesoporous organic polymer (HMOP) with nanorod morphology together with large BET surface area ~1218 m2 g?1, huge pore volumeγτ“;6 mL g?1 and dual micro/mesopore architectures. Subsequent Cu-coordination with nitrogen atoms of the HMOP provides a robust catalyst (Cu-HMOP) to accomplish multi-step cascade reactions for preparation of N-heterocycles by different routes. For instance, the Cu-HMOP efficiently catalyzes one-pot sequential multi-step oxidative dehydrogenative coupling of 2-aminobenzyl alcohol with diverse aromatic ketones to afford corresponding quinolines in excellent isolated yields (up to 97 %). Secondly, the present catalyst exhibits good aerobic oxidative dehydrogenation activity of amines to imines. Thirdly, for “click” reaction involving azides-alkynes, the Cu-HMOP produced quantitative yield for 1,4-disubstituted 1,2,3-triazole derivatives at room temperature using water as solvent. Verification of active metal leaching by a hot filtration test as well as reusability of the retrieved Cu-HMOP catalysts shows a consistent activity in the multi-component quinoline synthesis as model reaction.
- Elavarasan, Samaraj,Bhaumik, Asim,Sasidharan, Manickam
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p. 4340 - 4350
(2019/08/12)
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- Sustainable synthesis of N-heterocycles in water using alcohols following the double dehydrogenation strategy
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The present study describes the first example of synthesis of pharmaceutically relevant N-heterocycles like substituted quinolines, acridines and 1,8-naphthyridines in water under air using alcohols in presence of a new water soluble Ir-complex. The viability and efficiency of this approach was demonstrated by the efficient synthesis of biologically active natural product (±)-galipinine and gram scale synthesis of various N-heteroaromatics. Several kinetic experiments and DFT calculations were carried out to support the plausible reaction mechanism which disclosed that this system followed a concerted outer sphere mechanism for the dehydrogenation of alcohols.
- Maji, Milan,Chakrabarti, Kaushik,Panja, Dibyajyoti,Kundu, Sabuj
-
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- The Diverse One-Pot Reactions of 2-Quinolylzincates: Homologation, Electrophilic Trapping, Hydroxylation, and Arylation Reactions
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2-Quinolylzincates were efficiently produced from the regioselective metalation reactions of quinoline with various organozincates as key intermediates. The four different types of title reactions of these intermediates under the presented reaction conditions allowed for the facile formation of the corresponding C-2 functionalized quinolines, which are not successfully accessed through typical zincation methods.
- Jeong, Hye Jin,Chae, Suyeon,Jeong, Keunhong,Namgoong, Sung Keon
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supporting information
p. 6343 - 6349
(2018/10/31)
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- Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives
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A new phosphine-free Co(ii) complex-catalyzed synthesis of various quinoxalines via dehydrogenative coupling of vicinal diols with both o-phenylenediamines and 2-nitroanilines is reported. This complex was also effective for the synthesis of quinolines. The practical aspect of this catalytic system was revealed by the one-pot synthesis of 2-alkylaminoquinolines.
- Shee, Sujan,Ganguli, Kasturi,Jana, Kalipada,Kundu, Sabuj
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supporting information
p. 6883 - 6886
(2018/06/26)
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- 2-arylquinoline synthesis from Cbz-protected 2-aminochalcone mediated by BF3.Et2O
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A novel approach to producing the quinoline skeleton from 2-aminochalcone was developed. Treatment of benzyloxycarbonyl (Cbz)-protected 2-aminochalcones with BF3Et2O afforded quinoline derivatives via the deprotection of the Cbz group and isomerization of olefin in a one-pot reaction. The reaction of various 2-aminochalcones proceeded to give the corresponding 2-arylquinoline derivatives in good yields. This method is applicable to the rapid synthesis of dubamine.
- Maegawa, Tomohiro,Nogata, Misa,Honda, Takaya,Nakamura, Akira,Miki, Yasuyoshi
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p. 608 - 614
(2019/05/21)
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- Aryl and heteroaryl nosylates as stable and cheap partners for Suzuki-Miyaura cross-coupling reactions
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Aryl and heteroaryl para-nitrophenylsulfonates (nosylates) have been successfully engaged for the first time in Suzuki-Miyaura cross-coupling reactions with various aryl or vinylboronic acids (48-98%, 12 examples). The best catalyst/ligand combination have been determined to be 2 mol % of palladium acetate (Pd(OAc)2) and 4 mol % of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) using K3PO4 as base, in tetrahydrofuran at 80 °C. These new reaction conditions notably provide a direct and very efficient access to the natural alkaloid dubamine.
- Dikova, Anna,Cheval, Nicolas P.,Blanc, Aurélien,Weibel, Jean-Marc,Pale, Patrick
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p. 1960 - 1968
(2016/04/05)
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- Revealing the Macromolecular Targets of Fragment-Like Natural Products
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Fragment-like natural products were identified as ligand-efficient chemical matter for hit-to-lead development and chemical-probe discovery. Relying on a computational method using a topological pharmacophore descriptor and a drug database, several macromolecular targets from distinct protein families were expeditiously retrieved for structurally unrelated chemotypes. The selected fragments feature structural dissimilarity to the reference compounds and suitable target affinity, and they offer opportunities for chemical optimization. Experimental confirmation of hitherto unknown macromolecular targets for the selected molecules corroborate the usefulness of the computational approach and suggests broad applicability to chemical biology and molecular medicine. Target acquired: Hitherto unknown macromolecular targets of the fragment-like natural products goitrin, isomacroin, and graveolinine were discovered through the use of a computational target-prediction tool tailored for natural products. The results suggest that such methods will find application in target discovery for natural products and could inspire the design of new chemical entities for chemical biology and molecular medicine.
- Rodrigues, Tiago,Reker, Daniel,Kunze, Jens,Schneider, Petra,Schneider, Gisbert
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p. 10516 - 10520
(2015/09/02)
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- An efficient synthesis of quinolines via copper-catalyzed C-N cleavage
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An efficient method to synthesize substituted quinolines from ketones and 2-amino benzylamines is described. Copper-catalyzed C-N cleavage of amines followed by condensation with ketones deliver quinolines in moderate to high yields. The broad scope of su
- Xi, Long-Yi,Zhang, Ruo-Yi,Zhang, Lei,Chen, Shan-Yong,Yu, Xiao-Qi
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p. 3924 - 3930
(2015/03/30)
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- Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
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A series of diverse simple C2-aryl quinolines was synthesized de novo via a straightforward synthesis based on the acid-catalyzed multicomponent imino Diels-Alder reactions. Seven selected quinolines were evaluated at different stages of Leishmania braziliensis parasite. Among them, the 6-ethyl-2- phenylquinoline 5f was able to inhibit the growth of promastigotes of this parasite without affecting the mammalian cells viability and decreasing the number of intracellular L. braziliensis amastigotes on BMDM macrophages. The mechanism of action studied for the selected compound consisted in: (1) alteration of parasite bioenergetics, by disrupting mitochondrial electrochemical potential and alkalinization of acidocalcisomes, and (2) inhibition of ergosterol biosynthetic pathway in promastigote forms. These results validate the efficiency of quinoline molecules as leishmanicide compounds.
- Bompart, Daznia,Nú?ez-Durán, Jorge,Rodríguez, Daniel,Kouznetsov, Vladimir V.,Meléndez Gómez, Carlos M.,Sojo, Felipe,Arvelo, Francisco,Visbal, Gonzalo,Alvarez, Alvaro,Serrano-Martín, Xenón,García-Marchán, Yael
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p. 4426 - 4431
(2013/07/27)
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- Vinyl nosylates: An ideal partner for palladium-catalyzed cross-coupling reactions
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In a hurry to leave! Nosylates act as an excellent leaving group in various palladium-catalyzed cross-couplings, such as Suzuki, Stille, Heck, and Sonogashira reactions (see scheme). Crystalline, stable, and cheap vinyl and aryl nosylates proved better th
- Cheval, Nicolas P.,Dikova, Anna,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick
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supporting information
p. 8765 - 8768
(2013/07/26)
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- An efficient class of P,N-type "phMezole-phos" ligands: Applications in palladium-catalyzed Suzuki coupling of aryl chlorides
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This study describes an efficient class of hemilabile benzimidazolyl- phosphane ligands that can be easily accessed from commercially available and inexpensive starting materials. The application of this ligand array in the palladium-catalyzed Suzuki-Miyaura coupling reaction of aryl chlorides with arylboronic acids is described. The palladium catalyst generated from this hemilabile phosphane is highly effective in the Suzuki-Miyaura coupling of unactivated aryl chlorides, and catalyst loadings as low as 1 ppm can be achieved. An efficient class of hemilabile benzimidazolyl-phosphane ligands were synthesized. The palladium catalyst generated from this hemilabile phosphane is highly effective in the Suzuki-Miyaura coupling of unactivated aryl chlorides, and catalyst loadings as low as 1 ppm can be achieved.
- Wong, Shun Man,So, Chau Ming,Chung, Kin Ho,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 4172 - 4177
(2012/09/21)
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- Iron-catalyzed cross-coupling of N-heterocyclic chlorides and bromides with arylmagnesium reagents
-
A simple, practical iron salt catalyzed procedure allows fast cross-couplings of N-heterocyclic chlorides and bromides with various electron-rich and -poor arylmagnesium reagents. A solvent mixture of THF and tBuOMe is found to be essential for achieving high yields mainly by avoiding homocoupling side reactions.
- Kuzmina, Olesya M.,Steib, Andreas K.,Knochel, Paul,Flubacher, Dietmar
-
supporting information
p. 4818 - 4821,4
(2012/12/12)
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- Highly selective metalations of pyridines and related heterocycles using new frustrated lewis pairs or tmp-zinc and tmp-magnesium bases with bf 3·oet2
-
(Figure Presented) Efficient and selective: Frustrated Lewis pairs based on BF3·OEt2 and LiCl-com-plexed tmpMg or tmpZn amides (tmp = 2,2,6,6-tetramethylpiperidyl) allow the efficient and regioselective metalation of various functionalized N heterocycles (see scheme for examples). Moreover, such metalations carried out in the presence or absence of BF 3·OEt2 enable a complete switch of regioselectivity, thus allowing complementary fuctionalization.
- Jaric, Milica,Haag, Benjamin A.,Unsinn, Andreas,Karaghiosoff, Konstantin,Knochel, Paul
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supporting information; experimental part
p. 5451 - 5455
(2010/09/16)
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- One-pot friedlnder quinoline synthesis: Scope and limitations
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A highly effective one-pot Friedlnder quinoline synthesis from o-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The o-nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid; the amino compounds were then condensed in situ with ketones or aldehydes to form mono- or disubstituted quinolines, respectively, in good-to-excellent yields (58-100%). Georg Thieme Verlag Stuttgart - New York.
- Li, An-Hu,Beard, David J.,Coate, Heather,Honda, Ayako,Kadalbajoo, Mridula,Kleinberg, Andrew,Laufer, Radoslaw,Mulvihill, Kristen M.,Nigro, Anthony,Rastogi, Pawan,Sherman, Dan,Siu, Kam W.,Steinig, Arno G.,Wang, Ti,Werner, Doug,Crew, Andrew P.,Mulvihill, Mark J.
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experimental part
p. 1678 - 1686
(2010/06/22)
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- In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels-Alder reactions
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Diverse polyfunctionalized quinolines, easily prepared using Lewis acid-catalyzed imino Diels-Alder reactions between corresponding aldimines, were tested for antifungal properties against standardized as well as clinical isolates of clinically important fungi. Among them, 4-pyridyl derivatives displayed the best activities mainly against dermatophytes. The activity appears not to be related neither to the lipophilicity nor to the basicity of compounds.
- Melendez Gomez, Carlos M.,Kouznetsov, Vladimir V.,Sortino, Maximiliano A.,Alvarez, Sandra L.,Zacchino, Susana A.
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experimental part
p. 7908 - 7920
(2009/04/11)
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- Nickel-catalyzed cross-coupling reactions of aryltitanium(IV) alkoxides with aryl halides
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A nickel-catalyzed cross-coupling reaction between aryltitanium(IV) alkoxides and various functionalized aryl halides is described. The reaction requires Ni(acac)2 (0.5 mol%), a phosphine or an N-heterocyclic carbene ligand (NHC ligand; 0.5-1.0 mol%) and proceeds at 25°C within 1-24 hours. Georg Thieme Verlag Stuttgart.
- Manolikakes, Georg,Dastbaravardeh, Navid,Knochel, Paul
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p. 2077 - 2080
(2008/02/09)
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- Short step synthesis of natural 2-arylquinolones based on iridium-catalyzed three-component coupling quinoline synthesis
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Eduline (la), graveoline (1b), and 6-methoxy-2-(4-methoxyphenyl)-1-methylquinolone (1c) were synthesized by iridium-catalyzed three-component coupling reaction. Reaction of an aniline, an aromatic aldehyde, and acetaldehyde gave the corresponding substitu
- Nakajima, Takayuki,Inada, Takashi,Shimizu, Isao
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p. 497 - 504
(2008/02/03)
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- Nickel-catalyzed cyclization of 2-iodoanilines with aroylalkynes: An efficient route for quinoline derivatives
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An efficient and convenient nickel-catalyzed cyclization of 2-iodoanilines with alkynyl aryl ketones to give 2,4-disubstituted quinolines was developed. The reaction can be employed for the synthesis of naturally occurring quinoline derivatives in good yields. On the basis of the regiochemistry of the products, the possible pathway for the reaction is via the formation of o-aminochalcone.
- Korivi, Rajendra Prasad,Cheng, Chien-Hong
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p. 7079 - 7082
(2007/10/03)
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- Intramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines
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A thermally induced intramolecular annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined. The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used.
- S?derberg, Bj?rn C. G.,Shriver, James A.,Cooper, Seth H.,Shrout, Timothy L.,Helton, E. Scott,Austin, Lucinda R.,Odens, Herman H.,Hearn, Brian R.,Jones, Paula C.,Kouadio, Tiara N.,Ngi, Tan H.,Baswell, Rachel,Caprara, H. John,Meritt, Mark D.,Mai, Than T.
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p. 8775 - 8791
(2007/10/03)
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- Synthesis of 2-arylquinoline and 2-aryl-4-quinolone alkaloids via Diels- Alder reaction of 1,2,3-benzotriazine with enamines
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Synthesis of the 2-arylquinoline alkaloids, 2-phenylquinoline and dubamine, and the 2-arylquinolone alkaloids, 1-methyl-2-phenyl-4-quinolone, graveoline, reevesianine-A, and eduline, was accomplished by the Diels-Alder reaction of 1,2,3-benzotriazine with enamines as a key step.
- Koyama, Junko,Toyokuni, Izumi,Tagahara, Kiyoshi
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p. 1038 - 1039
(2007/10/03)
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- Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
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o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.
- Mahanty, Jyan S.,De, Mahuya,Das, Palas,Kundu, Nitya G.
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p. 13397 - 13418
(2007/10/03)
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- Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides
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The palladium-catalysed cross-coupling reactions of arylboronic acids with a variety of π-deficient heteroaryl chlorides proceed in high yield. [1,4-Bis(diphenylphosphino)butane]palladium(II) dichloride was found to be a very satisfactory catalyst for monocyclic heteroaryl chlorides, whereas tetrakis(triphenylphosphine)palladium(O) was found to be excellent for a range of chloroquinoline derivatives.
- Ali,McKillop,Mitchell,Rebelo,Wallbank
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p. 8117 - 8126
(2007/10/02)
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- APPLICATION OF THE LEWIS ACID CATALYZED CYCLOADDITION REACTION TO SYNTHESIS OF NATURAL QUINOLINE ALKALOIDS
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Lewis acids catalyzed cycloaddition reaction of the Schiff base with the olefin was applied to the syntheses of some natural quinoline alkaloids.The extension of cycloaddition using the acetal and the orthoester as dienophiles or using s-triazin
- Kametani, Tetsuji,Takeda, Hajime,Suzuki, Yukio,Kasai, Hiroko (nee Furuyama),Honda, Toshio
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p. 3385 - 3395
(2007/10/02)
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- A SIMPLE REGIOSELECTIVE PREPARATION OF 2- OR 3-SUBSTITUTED QUINOLINE DERIVATIVES VIA DIALKYLQUINOLYLBORANES
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Various quinoline derivatives possessing a substituent at the 2- or 3-position were prepared by the reaction of dialkylquinolylboranes and organic bromides in the presence of a palladium catalyst.
- Ishikura, Minoru,Oda, Izumi,Terashima, Masanao
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p. 2375 - 2386
(2007/10/02)
-