Issue 28, 2023

Convenient synthesis of N-alkyl-3,1-benzoxazin-2-ones from carbamate protected anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement

Abstract

A practical and step-economical protocol was developed to prepare N-alkyl-3,1-benzoxazin-2-one derivatives from anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement, where three new chemical bonds and one ring were constructed in a single step. Control studies revealed a stepwise mechanism and that the alkoxy rearrangement was an intermolecular process.

Graphical abstract: Convenient synthesis of N-alkyl-3,1-benzoxazin-2-ones from carbamate protected anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
23 May 2023
Accepted
28 Jun 2023
First published
28 Jun 2023
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2023,21, 5757-5761

Convenient synthesis of N-alkyl-3,1-benzoxazin-2-ones from carbamate protected anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement

G. Tian, W. Jin, C. Qin and J. Wang, Org. Biomol. Chem., 2023, 21, 5757 DOI: 10.1039/D3OB00812F

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