A Rearrangement of 4-Phenylbenzo[d]oxazoles to Phenanthridin-4-ols-Reference-Cited by-同舟云学术

A Rearrangement of 4-Phenylbenzo[d]oxazoles to Phenanthridin-4-ols

Published:2023-10-17 Issue:03 Volume:56 Page:507-517
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Fisyuk Alexander S.¹²^ORCID,Shatsauskas Anton L.¹,Keyn Ekaterina S.²,Stasyuk Anton J.³,Kirnosov Sergey A.²,Shuvalov Vladislav Yu.¹,Kostyuchenko Anastasia S.¹

Affiliation:

1. Laboratory of New Organic Materials, Omsk State Technical University

2. Department of Organic and Analytical Chemistry, Omsk F. M. Dostoevsky State University

3. Institut de Química Computacional and Departament de Química, Universitat de Girona

Abstract

AbstractA 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.

Funder

Russian Science Foundation

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-2193-5593.pdf

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