A rearrangement of 4-phenylbenzo[d]oxazoles to phenanthridin-4-ols

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Synthesis-Stuttgart Pub Date : 2023-10-17 DOI:10.1055/a-2193-5593

Alexander S. Fisyuk, Anton L. Shatsauskas, Anton J. Stasyuk, Vladislav Shuvalov, Anastasia S. Kostyuchenko, Sergey A. Kirnosov, Ekaterina S. Keyn

引用次数: 0

Abstract

A new approach was developed for the synthesis of phenanthridin-4-ols and 4-hydroxyphenanthridin-6(5H)-one derivatives in 43–89% yields based on the AlCl3-mediated rearrangement of available 4-phenylbenzo[d]oxazoles and 4-phenyl-1,3-benzoxazol-2(3H)-one. The quantum chemical calculations were used to describe the mechanism and predict the thermodynamic parameters of the reaction under study.

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4-苯基苯并[d]恶唑重排为4-菲蒽啶醇

利用alcl3介导的4-苯基苯并[d]恶唑和4-苯基1,3-苯并恶唑-2(3H)- 1的重排，以43-89%的产率合成了4-羟基菲蒽啶-4-醇和4-羟基菲蒽啶-6(5H)- 1衍生物。利用量子化学计算来描述反应机理和预测反应的热力学参数。

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

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.