Construction of New Heterocyclic System, Imidazo[4,5-d]thiazolo[4,3-b]oxazole, via Cascade Reaction of Thioglycolurils with α-Bromoketones

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-08-08 DOI:10.1002/ajoc.202400369

Ekaterina E. Vinogradova, Valentina A. Karnoukhova, Prof. Angelina N. Kravchenko, Dr. Galina A. Gazieva

引用次数: 0

Abstract

A method for the synthesis of new heterocyclic system representatives, i. e. imidazo[4,5-d]thiazolo[4,3-b]oxazole derivatives, by the reaction of thioglycolurils with α-bromoketones has been developed. The reaction includes a cascade one-pot S-alkylation/nucleophilic addition/ring-opening/ring-closing process. This protocol is compatible with a broad scope of α-bromoketones, diastereoselectively affording diverse products with 3aS*,4aR*,8aR*-imidazo[4,5-d]thiazolo[4,3-b]oxazole core in 40–76 % yields.

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通过硫代甘氨酰与α-溴酮的级联反应构建新的杂环系统--咪唑并[4,5-d]噻唑并[4,3-b]恶唑

本研究开发了一种通过硫代甘氨酰与α-溴酮反应合成新杂环体系代表物（即咪唑并[4,5-d]噻唑并[4,3-b]恶唑衍生物）的方法。该反应包括一个级联单锅 S-烷基化/亲核加成/环开环/环闭合过程。该方案兼容多种 α-溴酮，以 40-76% 的产率非对映选择性地得到以 3aS*,4aR*,8aR*-咪唑并[4,5-d]噻唑并[4,3-b]恶唑为核心的多种产物。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.