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

Autoren

  • 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
Weitere Informationen

Publikationsverlauf

Received: 08. März 2016

Accepted after revision: 31. März 2016

Publikationsdatum:
10. Mai 2016 (online)


Graphical Abstract

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