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Abstract <p>A method was developed for one-step preparing 5-(2-acylaminophenyl)-3-aryloxadiazoles by the reaction of amidoximes with benzoxazines, which does not require elevated temperatures and a long reaction time. Using a strong basic medium—a solution of NaOH in DMSO—allows for rapid condensation of the intermediately formed <i>O</i>-acylamidoximes at room temperature. Compared with a similar method for the synthesis of unsubstituted 5-(2-aminophenyl)oxadiazoles based on the isatoic anhydride reaction, the proposed one-step procedure not only makes it possible to obtain acyl derivatives of these amino heterocycles, but also reduces the reaction time 20-fold.</p>

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4H-3,1-Benzoxazin-4-ones Instead of Isatoic Anhydride: Reducing the Activity of the Substrate Allows You to Reduce the Synthesis Time

  • 期刊论文

  • 发表日期：

    2025年8月1日

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  • O. A. Gasilina,
  • A. A. Shetnev,
  • M. A. Alexeev,
  • M. V. Tarasenko,
  • S. V. Baykov,
  • E. V. Petersen,
  • V. P. Boyarskiy,
  • M. K. Korsakov

摘要

Abstract

A method was developed for one-step preparing 5-(2-acylaminophenyl)-3-aryloxadiazoles by the reaction of amidoximes with benzoxazines, which does not require elevated temperatures and a long reaction time. Using a strong basic medium—a solution of NaOH in DMSO—allows for rapid condensation of the intermediately formed O-acylamidoximes at room temperature. Compared with a similar method for the synthesis of unsubstituted 5-(2-aminophenyl)oxadiazoles based on the isatoic anhydride reaction, the proposed one-step procedure not only makes it possible to obtain acyl derivatives of these amino heterocycles, but also reduces the reaction time 20-fold.