Modeling stages of domino reaction of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate: a new synthetic route to γ-carbolines with thione group

IF 2.1 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Sulfur Chemistry Pub Date : 2024-05-03 DOI:10.1080/17415993.2023.2282667

Konstantin F. Suzdalev , Alina V. Krachkovskaya , Ekaterina A. Lysenko , Oleg P. Demidov

引用次数: 0

Abstract

Modeling stages of the cascade reaction of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate were studied. Alkylation of thiones with alkyl halides or dimethyl sulfate affording to thiopyrano[4,3-b]indole-2-ium salts models the first stage of the process. The attack at the 3-position of the obtained salts by secondary amines can serve as a model for the second stage of the cascade transformation; it gives 3-benzoylindoles with thioamide-group. Reactions of thiopyrano[4,3-b]indole-2-ium salts with primary amines lead to a series of γ-carbolines with thione group. The action of ammonia on these salts causes dealkylation and gives thiopyrano[4,3-b]indole-3(5H)-thiones.

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硫代吡喃并[4,3-b]吲哚-3(5H)-硫酮与乙炔二甲酸二甲酯多米诺反应的模型阶段：含硫酮基γ-咔啉的新合成路线

研究了硫代吡喃并[4,3-b]吲哚-3(5H)-亚硫酰与乙炔二甲酸二甲酯级联反应的模型阶段。硫酮与烷基卤化物或硫酸二甲酯发生烷基化反应，生成硫代吡喃并[4,3-b]吲哚-2-鎓盐，这是反应过程的第一阶段。仲胺攻击所得盐的 3 位，可以作为级联转化第二阶段的模型；它可以得到带有硫代酰胺基团的 3-苯甲酰基吲哚。硫代吡喃并[4,3-b]吲哚-2-鎓盐与伯胺的反应会产生一系列带有硫酮基的γ-咔啉。氨对这些盐的作用会导致脱烷基化，并产生硫代吡喃并[4,3-b]吲哚-3(5H)-硫酮。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.