由三氟甲基（烯基）酮和对甲基异氰酸酯合成5-三氟甲基-4,5-二氢恶唑

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2026-04-01 Epub Date: 2026-04-29 DOI:10.1002/ajoc.70393

Alexey R. Romanov , Vyacheslav V. Filatov , Sergey V. Zinchenko , Stepan A. Ukhanev

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引用次数: 0

摘要

介绍了一种合成5-（三氟甲基）-4,5-二氢恶唑的简便方法。为此，采用三氟甲基（烯基）酮与对甲苯基甲基异氰酸酯（TosMIC）在碱存在下的反应，获得了高收率的目标杂环。该工艺具有高度立体选择性和化学选择性。结合核磁共振和量子化学计算方法，明确证明了4,5-二氢恶唑的立体化学性质。恶唑环的形成是通过TosMIC对羰基部分的亲核攻击，然后在异氰化物片段的参与下进行分子内环化。

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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Synthesis of 5‐Trifluoromethyl‐4,5‐dihydrooxazoles From Trifluoromethyl(alkenyl)ketones and p‐Tosylmethylisocyanide

A simple synthetic approach towards 5‐(trifluoromethyl)‐4,5‐dihydrooxazoles was elaborated. To this end, the reaction of trifluoromethyl(alkenyl)ketones with p‐tosylmethylisocyanide (TosMIC) in the presence of the base was employed to afford the target heterocycles in good to high yields. The process is characterized by high stereo‐ and chemoselectivity. The stereochemistry of the 4,5‐dihydrooxazoles is unambiguously proved by the combination of NMR and quantum chemical calculational methods. The formation of the oxazole cycle occurs via nucleophilic attack of TosMIC on the carbonyl moiety, followed by intramolecular cyclization with participation of the isocyanide fragment.

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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.