- (S)-(-)-2-tert-butyl-3-methylene-oxirane: Synthesis and hydroboration of a chiral allene oxide
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The chiral allene oxide, (S)-(-)-2-tert-butyl-3-methylene-oxiran 12 ((S)-(-)-1-tert-butylallene oxide) was prepared in a moderate yield and in high enantiomeric excess by a three-step conversion starting from 4,4-dimethyl-2-pentyn-1-ol 6. The procedure wa
- Konoike,Hayashi,Araki
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Read Online
- RECEPTOR INHIBITOR, PHARMACEUTICAL COMPOSITION COMPRISING SAME, AND USE THEREOF
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The present invention discloses a receptor inhibitor of formula (I), a pharmaceutical composition comprising the same and the use thereof.
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Paragraph 0161-0162
(2021/01/28)
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- Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde
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A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.
- Huo, Xiaoli,Chen, Xiaojuan,Yu, Liya,Zhang, Chong,Zeng, Linghui,Zhu, Huajian,Shao, Jiaan,Fu, Liping,Zhang, Jiankang
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supporting information
p. 16430 - 16433
(2021/10/01)
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- Synthesis of Axially Chiral Styrenes through Pd-Catalyzed Asymmetric C?H Olefination Enabled by an Amino Amide Transient Directing Group
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The atroposelective synthesis of axially chiral styrenes remains a formidable challenge due to their relatively lower rotational barriers compared to the biaryl atropoisomers. Herein, we describe the construction of axially chiral styrenes through Pd
- Jin, Liang,Li, Ya,Liu, Lei,Liu, Yan-Hua,Shi, Bing-Feng,Song, Hong,Yao, Qi-Jun
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supporting information
p. 6576 - 6580
(2020/03/10)
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- Butenolide synthesis from functionalized cyclopropenones
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A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.
- Nguyen, Sean S.,Ferreira, Andrew J.,Long, Zane G.,Heiss, Tyler K.,Dorn, Robert S.,Row, R. David,Prescher, Jennifer A.
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supporting information
p. 8695 - 8699
(2019/10/28)
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- Gold(i)-catalyzed pathway-switchable tandem cycloisomerizations to indolizino[8,7-: B] indole and indolo[2,3-a] quinolizine derivatives
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Experimental and theoretical explorations were performed on the pathways of the cascade cycloisomerizations of tryptamine-N-ethynylpropiolamide substrates. The methodology provided a common strategy to access either indolizino[8,7-b]indoles or indolo[2,3-
- Liu, Chengjun,Sun, Zenghui,Xie, Fukai,Liang, Guoduan,Yang, Lu,Li, Yaqiao,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
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supporting information
p. 14418 - 14421
(2019/12/05)
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- Sodium Phenoxide Mediated Hydroxymethylation of Alkynylsilanes with N-[(Trimethylsiloxy)methyl]phthalimide
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The hydroxymethylation of alkynylsilanes with formaldehyde generated in situ from N-[(trimethylsiloxy)methyl]phthalimide proceeds in the presence of a stoichiometric amount of NaOPh. The reaction occurs at room temperature by using an operationally simple one-step procedure. A variety of alkynylsilanes possessing electron-donating, electron-withdrawing, and halogen groups (including heteroaryl-substituted alkynylsilanes) provide hydroxymethylated products.
- Asano, Narumi,Sasaki, Keita,Chataigner, Isabelle,Shigeno, Masanori,Kondo, Yoshinori
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supporting information
p. 6926 - 6930
(2017/12/26)
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- HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME
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Disclosed are compounds of formula (I): or a pharmaceutically acceptable salt thereof; wherein Y, Ra, Ra', Rc, Rf, X2, Rd, Rd', Re, Re', m, and G have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry, useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular and neurodegenerative diseases or disorders.
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Paragraph 00227
(2015/01/16)
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- BRIDGED BICYCLIC AMINO THIAZINE DIOXIDE COMPOUNDS AS INHIBITORS OF BETA-SECRETASE AND METHODS OF USE THEREOF
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The present invention provides a new class of compounds useful for the modulation of beta-secretase enzyme (BACE) activity. The compounds have a general Formula I: wherein variables A4, A5, A6, A8, R1, R2, R3, R7 and n of Formula I, independently, are defined herein. The invention also provides pharmaceutical compositions comprising the compounds, and corresponding uses of the compounds and compositions for treatment of disorders and/or conditions related to A-beta plaque formation and deposition, resulting from the biological activity of BACE. Such BACE mediated disorders include, for example, Alzheimer's Disease, cognitive deficits, cognitive impairments, schizophrenia and other central nervous system conditions. The invention further provides compounds of Formula II and sub-formula embodiments thereof, compounds of Formula III, intermediates and processes and methods useful for the preparation of compounds of Formulas I-III, and sub-Formulas thereof.
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Paragraph 0885; 0886
(2015/02/19)
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- Substrate scope and stereocontrol in the Rh(II)-catalysed oxyamination of allylic carbamates
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Application of a modified Du Bois protocol for rhodium-stabilised nitrenoid generation to a variety of allylic carbamates results in 4-acetoxymethyl-1,3-oxazolidin-2-one derivatives with moderate to high levels of stereocontrol.
- Unsworth, William P.,Lamont, Scott G.,Robertson, Jeremy
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p. 7388 - 7394
(2017/09/12)
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- SUBSTITUTED 4-AMINOBENZAMIDES AS KCNQ2/3 MODULATORS
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The invention relates to substituted 4-aminobenzamides, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 127; 128
(2013/11/05)
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- SUBSTITUTED 4-AMINOBENZAMIDES AS KCNQ2/3 MODULATORS
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Substituted 4-aminobenzamides, pharmaceutical compositions containing these compounds and also methods of using these compounds in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Paragraph 0649
(2013/11/05)
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- HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE
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The present invention relates to heterocyclic compounds useful for antagonising angiotensin II Type 2 (AT2) receptor. More particularly the invention relates to piperidine compounds, compositions containing them and their use in methods of treating or preventing disorders or diseases associated with AT2 receptor function including neuropathic pain, inflammatory pain, conditions associated with neuronal hypersensitivity, impaired nerve conduction velocity, cell proliferation disorders, disorders associated with an imbalance between bone resorption and bone formation and disorders associated with aberrant nerve regeneration.
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Page/Page column 88-89
(2013/08/15)
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- Reactivity pattern of bis(propargyloxy) disulfides: Tandem rearrangements and cyclizations
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Thirty-five substituted bis(propargyloxy) disulfides were successfully prepared in good to excellent yields, and their reactivity was found to be strongly dependent on the substitution pattern of the reactant. Inter alia they undergo surprising tandem sigmatropic rearrangements and cycloadditions. Three heretofore unknown product types were isolated and fully characterized: 6,7-dithiabicyclo[3.1.1]heptan-2-one 6-oxide derivatives, two isomeric 1,2-dithiete 1,1-dioxides (α,β-unsaturated four-membered cyclic thiosulfonates) from bis(propargyloxy) disulfides with α- or γ-alkyl-substituted propargyl groups, and two isomeric 2-oxa-5,7-dithiabicyclo[2.2.1]heptane 5-oxides from bis(propargyloxy) disulfides with α-tert-butyl- or α,α-dialkyl-substituted propargyl groups. Georg Thieme Verlag Stuttgart - New York.
- Braverman, Samuel,Pechenick-Azizi, Tatiana,Gottlieb, Hugo E.,Sprecher, Milon
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experimental part
p. 1741 - 1750
(2011/07/09)
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- Formation of isoxazolidines by enantioselective copper-catalyzed annulation of 2-nitrosopyridine with allylstannanes
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Click! Formal [3+2] cycloadditions of 2-nitrosopyridine with various allylstannanes give 4-stannyl-substituted isoxazolidines. The use of [Cu(MeCN)4]PF6, in combination with a Walphos ligand, leads to excellent enantioselectivies and high yields. With cis-2- alkenylstannanes as nucleophiles, 3-alkyl-4-stannyl-substituted isoxazolidines are formed with excellent diastereo- and enantioselectivities. Copyright
- Chatterjee, Indranil,Froehlich, Roland,Studer, Armido
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supporting information; experimental part
p. 11257 - 11260
(2012/02/02)
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- Gold catalysed cyclisation reactions of 1,6-diynes triggered by the addition of methanol
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Further investigations on our recently discovered gold catalysed cyclisation reaction of 1,6-diynes are reported. By varying the steric and electronic nature of the alkyne substituents, the potentials and limitations of the new reaction have been identifi
- Sperger, Christian,Strand, Lilian H.S.,Fiksdahl, Anne
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experimental part
p. 7749 - 7754
(2010/10/21)
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- ORGANIC COMPOUNDS FOR APPLICATIONS IN BACTERIAL INFECTIONS TREATMENT
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The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of human diseases.
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Page/Page column 46-47
(2010/04/25)
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- NOVEL IMIDAZO[1,2-A]PYRIDINE AND IMIDAZO[1,2-B]PYRIDAZINE DERIVATIVES
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Imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine derivatives which inhibit Btk and are useful for the treatment of auto-immune and inflammatory diseases caused by aberrant B-cell activation, e.g. arthritis.
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Page/Page column 96
(2009/07/18)
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- Substituted 4-aminocyclohexane derivatives
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Substituted 4-aminocyclohexane derivatives having the formula I: [image] wherein R1-R4 are as described herein, methods for their preparation, medicinal products and pharmaceutical compositions containing these compounds and the use of substituted 4-amino
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Page/Page column 16
(2009/09/07)
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- Asymmetric synthesis of α-allenylglycines
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The coupling of the homocuprate of the bislactim ether of cyclo-(-L-Val-Gly-) (9) with primary propargyl halides produces the allenyl-substituted bislactim ethers 11 in a highly diastereoselective manner, whereas the alkylation of the lith-iated bislactim ether of cyclo-(-L-Val-Gly-) yields the proparg-yl-substituted bislactim ethers 12. Subsequent hydrolysis affords, after protection of the amino group, the methyl α- allenylglycinates 15, the α-allenylglycines 16, and the methyl α-propargylglycinates 17.
- Bucuroaia, Carmen,Groth, Ulrich,Huhn, Thomas,Klinge, Michael
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experimental part
p. 3605 - 3612
(2009/12/01)
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- An improved synthesis route to functionalized 2-alkyn-1-ylboronates: Useful intermediates for the preparation of α-allenic alcohols
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Functionalized 2-alkyn-1-ylboronates were successfully prepared in good yields by reacting various acyclic and cyclic (iodomethyl)boronates with various alkynyllithium salts. Amongst various (iodomethyl)boronates studied, 2-(iodomethyl)-1,3,2-dioxa-4,4,5,5-tetramethylborolane provided improved chemical yields of 2-alkyn-1-ylboronates with pyran- and triisopropylsilyl- substituted alkynyllithium salts. 2-Alkyn-1-ylboronate bearing an acid sensitive structure (pyran) was successfully synthesized which would be very difficult to achieve under previously reported reaction conditions. The exceptionally rapid rearrangement of the "ate" complex derived from the pinacol (iodomethyl)boronate, suppression of the side product formation, and the stability of the pinacol 2-alkyn-1-ylboronate are some of the notable merits of this protocol. This new procedure offers a simple and convenient alternative route to the existing methodologies, in terms of the milder reaction conditions, functional group compatibility, and the ease of the operation. The synthesis scope of this class of 2-alkyn-1-ylboronates was demonstrated by reacting the pinacol 2-alkyn-1-ylboronate with benzaldehyde, which yielded the α-allenic alcohol in good yield and regioselectivity.
- Roy, Chandra D.,Soundararajan, Raman,Brown, Herbert C.
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experimental part
p. 241 - 249
(2009/05/27)
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- A direct and stereocontrolled route to conjugated enediynes
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A unified synthetic route to 3-hex-en-1,5-diynes, a key building block found in many of the enediyne antitumor agents and designed materials, was developed. The method, which relies on a carbenoid coupling-elimination strategy is tolerant of a wide range of functionalities, and was applied to the synthesis of a variety of linear and cyclic enediynes. Reaction parameters can be adjusted to control stereoselectivity of the process, producing linear enediynes from 1:12 to >100:1 E:Z ratio, and in the case of cyclic enediynes, giving the exclusively Z C-9, C-10, or C-11 products. Key features of the process are the ready availability of precursors and the mildness and efficiency of the reaction. Application of the process in the design of materials precursors and preparation of enediyne antitumor agents are presented.
- Jones, Graham B.,Wright, Justin M.,Plourde, Gary W.,Hynd, George,Huber, Robert S.,Mathews, Jude E.
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p. 1937 - 1944
(2007/10/03)
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- Stereochemical control in the metallohalocarbenoid route to linear enediynes
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Methods for the stereoselective preparation and unmasking of disubstituted Z enediynes are reported. The origins of the unprecedented stereoselectivity of the process are uncovered.
- Wright, Justin M.,Jones, Graham B.
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p. 7605 - 7609
(2007/10/03)
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- A simple, convenient, general procedure for the synthesis of 2-alkyn-1-ylboronates.
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Representative 2-alkyn-1-ylboronates have been synthesized in good to excellent yields using the reaction of the newly available diisopropyl iodomethylboronate with alkynyllithiums generated in situ. Comparable yields are obtained from both acyclic and cyclic boronates. However, 2-(iodomethyl)-1,3,2-dioxa-4,4,5-tetramethylborolane gave superior yields with a wide variety of alkynyllithiums. This procedure offers a simple and convenient alternative route to existing methodologies in terms of the milder reaction condition and the ease of the operation.
- Brown, Herbert C.,Roy, Chandra Deo,Soundararajan, Raman
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p. 765 - 768
(2007/10/03)
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- General synthesis of 2-alkyn-1-ylboronates in excellent isomeric purity
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2-Alkyn-1-ylboronates have been synthesized successfully, in excellent isomeric purity, via the in situ homologation of alkyn-1-ylboronates with LiCH2I. The relative reactivities exhibited by various LiCH2X reagents (X = Cl; Br; I) are described.
- Soundararajan, Raman,Li, Guisheng,Brown, Herbert C.
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p. 8961 - 8964
(2007/10/02)
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- Electron Delocalisation and Stabilisation in Substituted Amino- and Hydroxypropynyl Radicals
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A series of aminopropynes, RCCCH2NH2 (R = H, Me, t-Bu, Me3Si), RCCCH2N(SiMe3)2, and hydroxypropynes RCCCH2OH (R = H, Me, t-Bu, Me3Si, CF3, and EtO2C), were prepared and the corresponding α-aminopropynyl and α-hydroxypropynyl radicals were examined by e.s.r. spectroscopy.For the first series, the C-N bond rotation barriers were determined from the exchange broadening in the spectra and hence radical stabilization energies were estimated.The spin distribution in these series indicated an extra delocalisation in radicals with captodative substitution.
- MacInnes, Iain,Walton, John C.
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p. 1077 - 1082
(2007/10/02)
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- Organoboranes. 38. A Facile and Highly Efficient Addition of B-1-Alkynyl-9-borabicyclononanes to Aldehydes and Ketones: An Exceptionally Chemoselective Synthesis of Propargylic Alcohols
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B-1-Alkynyl-9-borabicyclononanes (B-1-alkynyl-9-BBN) readily undergo addition to aldehydes and ketones and afford the propargylic alcohols in very high isolated yields.Unlike many other alkynyl metals (RCCM, M = Li, Na, K, Mg, Zn, and Al), which
- Brown, Herbert C.,Molander, Gary A.,Singh, Shankar M.,Racherla, Uday S.
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p. 1577 - 1582
(2007/10/02)
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