- Synthesis of peptide thioacids at neutral pH using bis(2-sulfanylethyl) amido peptide precursors
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Reaction of bis(2-sulfanylethyl)amido (SEA) peptides with triisopropylsilylthiol in water at neutral pH yields peptide thiocarboxylates. An alkylthioester derived from β-alanine was used to trap the released bis(2-sulfanylethyl)amine and displace the equi
- Pira, Silvain L.,Boll, Emmanuelle,Melnyk, Oleg
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- Catalytic Decarboxylative C?N Formation to Generate Alkyl, Alkenyl, and Aryl Amines
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Transition-metal-catalyzed sp2 C?N bond formation is a reliable method for the synthesis of aryl amines. Catalytic sp3 C?N formation reactions have been reported occasionally, and methods that can realize both sp2 and sp3 C?N formation are relatively unexplored. Herein, we address this challenge with a method of catalytic decarboxylative C?N formation that proceeds through a cascade carboxylic acid activation, acyl azide formation, Curtius rearrangement and nucleophilic addition reaction. The reaction uses naturally abundant organic carboxylic acids as carbon sources, readily prepared azidoformates as the nitrogen sources, and 4-dimethylaminopyridine (DMAP) and Cu(OAc)2 as catalysts with as low as 0.1 mol % loading, providing protected alkyl, alkenyl and aryl amines in high yields with gaseous N2 and CO2 as the only byproducts. Examples are demonstrated of the late-stage functionalization of natural products and drug molecules, stereospecific synthesis of useful α-chiral alkyl amines, and rapid construction of different ureas and primary amines.
- Zhang, Yipin,Ge, Xia,Lu, Hongjian,Li, Guigen
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supporting information
p. 1845 - 1852
(2020/12/01)
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- Highly efficient synthesis of silica-coated magnetic nanoparticles modified with iminodiacetic acid applied to synthesis of 1,2,3-triazoles
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Great efforts have been made to discover new catalysts to facilitate synthesis of organic fine chemicals. In this research, a new silica-coated magnetic nanoparticles functionalized by iminodiacetic acid (Fe3O4@SiO2@IDA) w
- Godarzbod, Farideh,Mirjafary, Zohreh,Saeidian, Hamid,Rouhani, Morteza
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- KRAS G12D INHIBITORS
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The present invention relates to compounds that inhibit KRas G12D. In particular, the present invention relates to compounds that inhibit the activity of KRas G12D, pharmaceutical compositions comprising the compounds and methods of use therefor.
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Paragraph 0248
(2021/03/05)
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- Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions
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Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.
- Chang, Sukbok,Jung, Hoimin,Kim, Dongwook,Lee, Jeonghyo,Lee, Jia,Park, Juhyeon
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p. 12324 - 12332
(2020/08/06)
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- Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature
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A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.
- Azeez, Sadaf,Chaudhary, Priyanka,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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supporting information
p. 6902 - 6907
(2018/10/02)
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- Copper(I)-Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Azidoformates and Aryl Terminal Alkynes
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The copper(I)-catalyzed azide-alkyne cycloaddition reaction has been extensively studied and widely applied in organic synthesis. However, the formation of 1,2,3-triazoles with electron-deficient azide has been a challenging problem. In this report, we ha
- Lee, Heejin,Lee, Jae Kyun,Min, Sun-Joon,Seo, Hyeonglim,Lee, Youngbok,Rhee, Hakjune
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p. 4805 - 4811
(2018/04/26)
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- The enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to isatin-derived ketimines
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An asymmetric organocatalytic addition of fluorinated phenylsulfonylnitromethane to isatin-derived ketimines was developed. The reaction was efficiently catalyzed by a chiral tertiary amine, cinchonine. This methodology provides a new type of optically active compound with two adjacent quaternary carbon stereocenters in good yield (up to 96%), with moderate diastereoselectivity (up to 5.7:1 dr) and excellent enantioselectivity (up to 98/96% ee).
- Urban,Franc,Hofmanová,Císa?ová,Vesely
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supporting information
p. 9071 - 9076
(2017/11/14)
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- Cesium Carboxylate-Promoted Iridium Catalyzed C-H Amidation/Cyclization with 2,2,2-Trichloroethoxycarbonyl Azide
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An Ir(III)-catalyzed direct C-H amidation/cyclization of benzamides using 2,2,2-trichloroethoxycarbonyl azide (TrocN3) as the aminocarbonyl source is reported. With the aid of cesium carboxylate, the reactions proceed efficiently and with high regioselectivity, producing various functionalized quinazoline-2,4(1H,3H)-diones, which are important building blocks and key synthetic intermediates for biologically and medicinally important compounds. During the reactions, two new C-N bonds were formed by breaking C-H and N-H bonds sequence.
- Zhang, Tao,Wang, Zhen,Hu, Xuejiao,Yu, Meng,Deng, Tianning,Li, Guigen,Lu, Hongjian
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p. 4898 - 4905
(2016/07/06)
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- An unexpected diethyl azodicarboxylate-promoted dehydrogenation of tertiaryamine and tandem reaction with sulfonyl azide
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It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives. Copyright
- Xu, Xiaoliang,Li, Xiaonian,Ma, Lei,Ye, Ning,Weng, Bojie
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supporting information; experimental part
p. 14048 - 14049
(2009/03/11)
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- An efficient one-pot synthesis of azidoformates from alcohols using triphosgene: Synthesis of N-carbobenzyloxy azetidin-2-ones
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An efficient use of triphosgene for the preparation of various azidoformates from alcohols and sodium azide is described. The method is applied to various chiral alcohols including glucose diacetonide to get the corresponding azidoformates. One of these azidoformates has been successfully utilized for the synthesis of N-carbobenzyloxy-β-lactams.
- Patil,Parveen, Ghazala,Gumaste,Bhawal,Deshmukh
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p. 1455 - 1458
(2007/10/03)
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- A facile synthesis of azidoformate via chloroformate
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This work synthesized chloroformates by slowly adding alcohols into a suspension of trichloromethyl chloroformate, instead of phosgene, along with activated charcoal in tetrahydrofuran. This chloroformylation yielded chloroformates in near quantitative yield. The subsequent reaction between chloroformates and sodium azide in dry acetone produced azidoformates in a high yield.
- Wu, Pei-Lin,Su, Chia-Hao,Gu, Yi-Jeng
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p. 271 - 274
(2007/10/03)
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