Synthesis 2019; 51(21): 4043-4057
DOI: 10.1055/s-0039-1690186
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Synthesis of Nitrones via Transition-Metal-Free Ring-Opening of N-Tosylaziridines with the Nitrogen Atom of Various (E)-Aldoximes and (E)-Ketoximes

Xing Li
Department of Biomedical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China   Email: lixing@tyut.edu.cn   Email: txp1963@sina.com
,
Wenjing Yan
,
Rui Zhang
,
Honghong Chang
,
Wenchao Gao
,
Xiuping Tian
Department of Biomedical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China   Email: lixing@tyut.edu.cn   Email: txp1963@sina.com
,
Wenlong Wei
› Author Affiliations
We appreciate gratefully the Natural Science Foundation of Shanxi Province (No. 201601D011028) for financial support.
Further Information

Publication History

Received: 03 June 2019

Accepted after revision: 29 July 2019

Publication Date:
22 August 2019 (eFirst)

Abstract

The KOH-, K2CO3-, or Et3N-catalyzed ring-opening reaction of N-tosylaziridines using the nitrogen atom of a series of (E)-aldoximes and (E)-ketoximes as a nucleophilic atom instead of an oxygen atom was developed to construct various nitrones under mild reaction conditions. Diverse (E)-aldoximes and (E)-ketoximes were demonstrated to be compatible with this reaction and the products of O-ring-opening reactions were not detected for most examples.

Supporting Information

 
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