Synthesis of 3-methyl-4H-benzo[b][1,4]thiazine-2-carboxylates using CAN as a catalyst and its conversion into guanidines.

IF 0.9 Q4 CHEMISTRY, PHYSICAL

Current Organocatalysis Pub Date : 2020-12-28 DOI:10.2174/2213337207999201228141906

Dhanaji V. Jawale, Devendra S. Wagare, D. Lingampalle, Prashant D. Netankar

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引用次数: 0

Abstract

1,4-benzothiazine carboxylates show wide application in the field of medicinal chemistry. Therefore, we have designed convenient and efficient method for the synthesis of 1,4-benzothiazine carboxylates. Synthesis of 1,4-benzothiazine carboxylates and its guanidines by simple and facile method using efficient catalyst. Derivatives of 1,4-benzothiazine carboxylates were synthesized by cyclocondensing β-keto esters with 2- aminobenzenethiols using CAN as a catalyst at room temperature. 1,4-benzothiazine caboxylate,condensed with guanidine hydrochloride in the presence of sodium methoxide in DMF to obtained new 3-substituted-l-4Hbenzo[b][1,4]thiazine-2-carboxyguanidines (88-91%). All the products were obtained with good to excellent yields within 40 min. Here, CAN oxidizes aminothiophenol into disulfide and then nucleophilic attack of enolic form of β-ketoesters on the disulphide and 1, 4-benzothiazine acetates, were obtained with good yields. We have designed convenient and efficient method for the synthesis of 1,4-benzothiazine carboxylates. Most remarkable features of this cyclocondensation such as use of efficient catalyst and non-volatile solvent under mild reaction condition to obtained excellent yield.

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以CAN为催化剂合成3-甲基-4H-苯并[b][1,4]噻嗪-2-羧酸盐及其转化为胍。

1,4-苯并噻嗪羧酸盐在药物化学领域有着广泛的应用。因此，我们设计了一种方便有效的合成1,4-苯并噻嗪羧酸盐的方法。高效催化剂催化合成1,4-苯并噻嗪羧酸盐及其胍类化合物。以CAN为催化剂，在室温下用2-氨基苯硫醇环缩合β-酮酯，合成了1,4-苯并噻嗪羧酸盐衍生物。1,4-苯并噻嗪甲氧基化物，在甲醇钠存在下在DMF中与盐酸胍缩合，得到新的3-取代-l-4Hbenzo[b][1,4]噻嗪-2-羧基胍（88-91%）。所有产物在40分钟内以良好至优异的产率获得，CAN将氨基硫酚氧化为二硫化物，然后得到烯醇形式的β-酮酯对二硫化物和1,4-苯并噻嗪乙酸酯的亲核攻击，产率很高。我们设计了一种简便有效的合成1,4-苯并噻嗪羧酸盐的方法。这种环缩合反应的主要特点是在温和的反应条件下使用了高效的催化剂和非挥发性溶剂，获得了优异的产率。

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来源期刊

Current Organocatalysis CHEMISTRY, PHYSICAL-

CiteScore

2.00

自引率

0.00%

发文量

期刊介绍： Current Organocatalysis is an international peer-reviewed journal that publishes significant research in all areas of organocatalysis. The journal covers organo homogeneous/heterogeneous catalysis, innovative mechanistic studies and kinetics of organocatalytic processes focusing on practical, theoretical and computational aspects. It also includes potential applications of organocatalysts in the fields of drug discovery, synthesis of novel molecules, synthetic method development, green chemistry and chemoenzymatic reactions. This journal also accepts papers on methods, reagents, and mechanism of a synthetic process and technology pertaining to chemistry. Moreover, this journal features full-length/mini review articles within organocatalysis and synthetic chemistry. It is the premier source of organocatalysis and synthetic methods related information for chemists, biologists and engineers pursuing research in industry and academia.