- An anhydride and β-azido disulfide simple new method for the synthesis of thiazole (by machine translation)
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This invention has offered a kind of direct to anhydride and β-azido disulfide as the substrate, in the neutral organic phosphine, organic alkali reagent and oxidation under the combined action of the reagent, one-pot synthesis of high-efficient synthesis of thiazole compound new method. As shown in general formula I, the method is simple in operation, economic, anhydride available for sale in the market as the substrate, under the mild alkaline conditions, there is no need to add any coupling reagent can be conveniently completed the synthesis of thiazole compounds. (by machine translation)
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Paragraph 0027-0033
(2017/03/14)
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- Concise synthesis of 2,4-disubstituted thiazoles from β-azido disulfides and carboxylic acids or anhydrides: Asymmetric synthesis of cystothiazole C
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A novel and efficient method for the one-pot synthesis of 2,4-disubstituted thiazoles from carboxylic acids or anhydrides is presented. Based on this new method, the total synthesis of the bis-2,4-disubstituted bis(thiazoles) natural product cystothiazole C is also presented. This journal is
- Liu, Yi,Sun, Xue,Zhang, Xing,Liu, Jun,Du, Yuguo
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p. 8453 - 8461
(2014/12/10)
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- Convenient Synthesis of Azolines to Azoles
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Azolines are oxidized in the presence of a copper-containing catalyst to azoles in the presence of molecular oxygen. A synthetic scheme converting azolines azoles is also provided.
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Paragraph 0102; 0112
(2013/03/26)
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- Copper-catalyzed oxidation of azolines to azoles
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We report herein convenient, aerobic conditions for the oxidation of thiazolines to thiazoles and data regarding the oxidation mechanism. These reactions feature operationally simple and environmentally benign conditions and proceed in good yield to afford the corresponding azoles, thus enabling the inexpensive preparation of valuable molecular building blocks. Incorporation of a novel diimine-ligated copper catalyst, [(MesDABMe) CuII(OH2)3]2+ [-OTf] 2, provides increased reaction efficiency in many cases. In other cases copper-free conditions involving a stoichiometric quantity of base affords superior results.
- Dawsey, Anna C.,Li, Vincent,Hamilton, Kimberly C.,Wang, Jianmei,Williams, Travis J.
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p. 7994 - 8002
(2012/08/08)
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- Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates
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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
- Théveau, Laure,Verrier, Cécile,Lassalas, Pierrik,Martin, Thibaut,Dupas, Georges,Querolle, Olivier,Van Hijfte, Luc,Marsais, Francis,Hoarau, Christophe
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supporting information; experimental part
p. 14450 - 14463
(2012/01/15)
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- Total synthesis of epothilones B and D: Stannane equivalents for β-keto ester dianions
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(Chemical Equation Presented) Studies leading to a total synthesis of epothilones B and D are described. The overall synthetic plan was based on late-stage fragment assembly of two segments representing C1-C 9 and C10-C21 of the structure. The C 1-C9 fragment was prepared by elaboration of commercially available (2R)-3-hydroxy-2-methylpropanoate at both ends of the three-carbon unit. Introduction of carbons 1-4 containing the gem-dimethyl unit was achieved in a convergent manner using a diastereoselective addition of a stannane equivalent of a β-keto ester dianion. An enantioselective addition of such a stannane equivalent for a β-keto ester dianion was also used to fashion one version of the C10-C21 subunit; however, the fragment assembly (using bimolecular esterification followed by ring-closing metathesis) with this subunit failed. Therefore, fragment assembly was achieved using a Wittig reaction; this was followed by macrolactonization to close the macrocycle. The C10-C21 subunit needed for this approach was prepared in an efficient manner using the Corey-Kim reaction as a key element. Other key reactions in the synthesis include a stereoselective SmI 2 reduction of a β-hydroxy ketone and a critical opening of a valerolactone with aniline which required extensive investigation.
- Keck, Gary E.,Giles, Robert L.,Cee, Victor J.,Wager, Carrie A.,Yu, Tao,Kraft, Matthew B.
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supporting information; experimental part
p. 9675 - 9691
(2009/04/07)
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- PIPERAZINES AND PIPERIDINES AS mGluR5 POTENTIATORS
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The invention relates to compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof: wherein Ar1, Ar2, A, X, Y, m, n and R1 to R5 are described in the specification.
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Page/Page column 67-68
(2008/06/13)
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- Asymmetric synthesis of 2-alkyl-3-thiazoline carboxylates: Stereochemistry of the MnO2-mediated oxidation of cis- and trans-2-alkyl-thiazolidine-(4R)-carboxylates
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The asymmetric synthesis of a series of 3-thiazoline carboxylates, 2, was effected by MnO2 oxidation of the corresponding cis/trans thiazolidines, 1. The stereochemistry of the oxidation reaction was studied using NMR and chiral GC analyses. Compounds 2 were obtained with enantiomeric excesses (e.e.s) in the range of 40-100%.
- Fernandez, Xavier,Duach, Elisabet
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p. 1279 - 1286
(2007/10/03)
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- Chemo- and regioselective synthesis of alkyl-3-thiazoline carboxylates
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The synthesis of a series of allyl substituted 3-thiazoline-carboxylates was carried out from the corresponding thiazolidines, by a MnO2-mediated oxidation reaction under mild conditions. The reaction was chemoselective towards the amine-imine oxidation and was also regioselective, affording the unsaturation at the 3-position of the heterocycle.
- Fernandez, Xavier,Fellous, Roland,Lizzani-Cuvelier, Louisette,Loiseau, Michel,Duach, Elisabet
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p. 1519 - 1521
(2007/10/03)
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