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Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

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Abstract

We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 °C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by using this synthetic protocol. Mechanistic experiments indicated that the hydroxy proton of the aminophenol could play a crucial role in the formation of an alkynylketimine intermediate that undergoes 7-endo-dig cyclization.

Graphical abstract: Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

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Submitted
13 Nov 2019
Accepted
17 Dec 2019
First published
18 Dec 2019

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

K. Oshimoto, B. Zhou, H. Tsuji and M. Kawatsura, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02450F

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