通过2-炔基硫代咪唑环化制备5-取代7h -咪唑[2,1-b][1,3]噻嗪的简单方法

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Synthesis-Stuttgart Pub Date : 2023-09-20 DOI:10.1055/a-2179-1250

Indrė Misiūnaitė, Raminta Bajarūnaitė, Rita Buksnaitiene, Algirdas Brukštus, Ieva Žutautė

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引用次数: 0

摘要

亲电引发的2-炔基噻吩并咪唑的亲核环化是合成新的杂环体系的有效手段。然而，卤素引发的环化反应在使用其他咪唑类似物的亲电加成和取代反应之间表现出较差的选择性。在本研究中，采用几种不同的造币金属催化剂，以原子经济的方式扩大了7h -咪唑[2,1-b][1,3]噻嗪的范围。以2-炔基硫代咪唑和AuCl为催化剂，在DCE/DCM中实现了6-内切途径的选择性反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Straightforward approach to 5-substituted 7H-imidazo[2,1-b][1,3]thiazines via cyclization of 2-alkynylthioimidazoles

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Straightforward approach to 5-substituted 7H-imidazo[2,1-b][1,3]thiazines via cyclization of 2-alkynylthioimidazoles

Electrophile-initiated nucleophilic cyclization of 2-alkynylthiobenzimidazoles is a useful tool for synthesizing new heterocyclic systems. However, halogen-initiated cyclization demonstrates poor selectivity between electrophilic addition and substitution reactions using other imidazole analogues. In this research, several different coinage-metal catalysts were employed to broaden the scope of 7H-imidazo[2,1-b][1,3]thiazines in atom-economic manner. Selective 6-endo-dig pathway reactions were achieved in good to excellent yields using various 2-alkynylthioimidazoles with AuCl as a catalyst in DCE/DCM.

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来源期刊

Synthesis-Stuttgart 化学-有机化学

CiteScore

4.50

自引率

7.70%

发文量

435

审稿时长

1 months

期刊介绍： SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.