99972-45-9Relevant articles and documents
One-pot four-component synthesis of polysubstituted thiazoles via cascade Ugi/Wittig cyclization starting from odorless Isocyano(triphenylphosphoranylidene)-acetates
Ding, Ming-Wu,Guan, Zhi-Rong,Liu, Zi-Ming,Wan, Qin
, (2020/03/23)
A new one-pot four-component preparation of polysubstituted thiazoles by a cascade Ugi/Wittig cyclization has been developed. The four-component reactions of the odorless isocyano(triphenylphosphoranylidene)acetates 1, aldehydes 2, amines 3 and thiocarboxylic acids 4 produced 2,4,5-trisubstituted thiazoles 5 in moderate to good yields in the presence of triethylamine. The two-component reactions between isocyano(triphenylphosphoranylidene)acetates 1 and thiocarboxylic acids 4 in the presence of triethylamine provided the corresponding 4,5-disubstituted thiazoles 6 in good yields as well.
Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates
Théveau, Laure,Verrier, Cécile,Lassalas, Pierrik,Martin, Thibaut,Dupas, Georges,Querolle, Olivier,Van Hijfte, Luc,Marsais, Francis,Hoarau, Christophe
supporting information; scheme or table, p. 14450 - 14463 (2012/01/15)
Both base-assisted non-concerted metallation-deprotonation (nCMD) and concerted metallation-deprotonation (CMD) have been identified as two potent operating mechanisms in palladium-catalysed direct C-H coupling of oxazole and thiazole-4-carboxylate esters
TRANS-3-AZA-BICYCLO[3.1.0]HEXANE DERIVATIVES
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Page/Page column 60, (2009/03/07)
The invention relates to novel trans-3-aza-bicyclo[3.1.0]hexane derivatives of formula (I), wherein A, B, n and R1 are as described in the description, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.
Direct C-2 arylation of alkyl 4-thiazolecarboxylates: New insights in synthesis of heterocyclic core of thiopeptide antibiotics
Martin, Thibaut,Verrier, Cecile,Hoarau, Christophe,Marsais, Francis
scheme or table, p. 2909 - 2912 (2009/05/30)
(Chemical Equation Presented) The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4- thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.
Identification of potent type I MetAP inhibitors by simple bioisosteric replacement. Part 1: Synthesis and preliminary SAR studies of thiazole-4-carboxylic acid thiazol-2-ylamide derivatives
Cui, Yong-Mei,Huang, Qing-Qing,Xu, Jie,Chen, Ling-Ling,Li, Jing-Ya,Ye, Qi-Zhuang,Li, Jia,Nan, Fa-Jun
, p. 3732 - 3736 (2007/10/03)
A series of thiazole-4-carboxylic acid thiazol-2-ylamide (TCAT, 4) derivatives were designed and synthesized according to simple bioisosteric replacement from previously reported pyridine-2-carboxylic acid thiazol-2-ylamide (PCAT) MetAP inhibitors. The preliminary SAR studies demonstrated that these TCAT series of compounds showed different activity and selectivity compared with those of the corresponding PCAT compounds. These findings provide useful information for the design and discovery of more potent inhibitors of type I MetAPs.
A Novel Synthesis of Methyl 5-Substituted Thiazole-4-carboxylates Using 3-Bromo-2-isocyanoacrylates (BICA)
Yamada, Masaki,Fukui, Toshio,Nunami, Ken-ichi
, p. 257 - 260 (2007/10/02)
A novel synthetic method for methyl 5-substituted thiazole-4-carboxylates (5) by the reaction of methyl 3-substituted 3-bromo-2-isocyanoacrylates (BICA) (1) with hydrogen sulfide in the presence of triethylamine in N,N-dimethylformamide was explored, and
