Direct Access to 2‐Aminobenzoxazinones via Ph 3 P‐I 2 Mediated Deoxygenative Amination of Isatoic Anhydrides with Tertiary Amines

Abstract A facile and efficient sonochemical synthesis of 2‐amino‐substituted benzoxazinones was achieved via Ph 3 P‐I 2 mediated deoxygenative amination of isatoic anhydrides. Tertiary amines play a dual role as bases and nucleophiles to react with a range of readily available isatoic anhydrides vi...

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Published inEuropean journal of organic chemistry Vol. 2022; no. 43
Main Authors Pattarawarapan, Mookda, Yamano, Dolnapa, Wiriya, Nittaya, Hongsibsong, Surat, Phakhodee, Wong
Format Journal Article
LanguageEnglish
Published 18.11.2022
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Summary:Abstract A facile and efficient sonochemical synthesis of 2‐amino‐substituted benzoxazinones was achieved via Ph 3 P‐I 2 mediated deoxygenative amination of isatoic anhydrides. Tertiary amines play a dual role as bases and nucleophiles to react with a range of readily available isatoic anhydrides via regioselective C2‐N bond formation N ‐dealkylation. Unlike secondary amines, competing side reaction at C4 carbonyl is completely circumvented. The reaction is also applicable to bicyclic amidines including DBU (1,8‐diazabicyclo[5.4.0]undec‐7‐ene) and DBN (1,5‐diazabicyclo[4.3.0]non‐5‐ene) providing ϵ‐caprolactam‐ and γ‐lactam derivatives, respectively.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202201069