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

Guang Tian; Wei-Li Jin; Chuanguang Qin; Jie Wang

doi:10.1039/d3ob00812f

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

Org Biomol Chem. 2023 Jul 19;21(28):5757-5761. doi: 10.1039/d3ob00812f.

Authors

Guang Tian^{1

2}, Wei-Li Jin^{3

2}, Chuanguang Qin¹, Jie Wang^{2

3

4}

Affiliations

¹ Department of Chemistry, Shanxi Key Laboratory of Polymer Science & Technology, MOE Key Laboratory of Supernormal Material Physics & Chemistry, School of Chemical & Chemical Engineering, Northwestern Polytechnical University, Xi'an 710129, China. qinchg@nwpu.edu.cn.
² State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. jiewang@simm.ac.cn.
³ School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China.
⁴ University of Chinese Academy of Sciences, Beijing 100049, China.

PMID: 37404025
DOI: 10.1039/d3ob00812f

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.