Synthesis 2016; 48(12): 1934-1938
DOI: 10.1055/s-0035-1561437
special topic
© Georg Thieme Verlag Stuttgart · New York

Triflic Anhydride Mediated Ring-Opening/Recyclization Reaction of α-Carbamoyl α-Oximyl Cyclopropanes with DMF: Synthetic Route to 5-Aminoisoxazoles

Mangfei Yu
a  School of Chemistry and Materials Science, Heilongjiang University, 74 Xuefu Road, Harbin 150080, P. R. of China   Email: yanpf@vip.sina.com
b  Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, P. R. of China   Email: dwdong@ciac.ac.cn
,
Qian Zhang
b  Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, P. R. of China   Email: dwdong@ciac.ac.cn
,
Jia Wang
b  Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, P. R. of China   Email: dwdong@ciac.ac.cn
,
Peng Huang
b  Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, P. R. of China   Email: dwdong@ciac.ac.cn
,
Pengfei Yan*
a  School of Chemistry and Materials Science, Heilongjiang University, 74 Xuefu Road, Harbin 150080, P. R. of China   Email: yanpf@vip.sina.com
,
Rui Zhang
b  Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, P. R. of China   Email: dwdong@ciac.ac.cn
,
Dewen Dong*
b  Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, P. R. of China   Email: dwdong@ciac.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 08 March 2016

Accepted after revision: 31 March 2016

Publication Date:
10 May 2016 (eFirst)

Abstract

A facile and efficient synthesis of fully substituted 5-amino­isoxazoles was developed from α-cyclopropyl β-oximyl amides in the presence of triflic anhydride (Tf2O) in DMF under very mild conditions. The process involves sequential ring-opening and intramolecular cyclization reactions.

Supporting Information

 
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