Download PDF
Synthesis 2018; 50(09): 1875-1882
DOI: 10.1055/s-0037-1609318
paper
© Georg Thieme Verlag Stuttgart · New York

PIFA-Mediated Oxidative Cyclization Reactions of α-Acyl Acrylamides: A Synthetic Route to Substituted Isoxazol-3(2H)-ones

Jingwen Yuan
a   Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China   Email: ariel@ciac.ac.cn   Email: dwdong@ciac.ac.cn
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. China
,
Chitturi Bhujanga Rao
a   Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China   Email: ariel@ciac.ac.cn   Email: dwdong@ciac.ac.cn
,
Qian Zhang
a   Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China   Email: ariel@ciac.ac.cn   Email: dwdong@ciac.ac.cn
,
Rui Zhang*
a   Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China   Email: ariel@ciac.ac.cn   Email: dwdong@ciac.ac.cn
,
Yongjiu Liang
a   Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China   Email: ariel@ciac.ac.cn   Email: dwdong@ciac.ac.cn
,
Ning Zhang
a   Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China   Email: ariel@ciac.ac.cn   Email: dwdong@ciac.ac.cn
,
Dewen Dong*
a   Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China   Email: ariel@ciac.ac.cn   Email: dwdong@ciac.ac.cn
› Author Affiliations
Financial support of this research by the National Natural Science Foundation of China (21502185 and 21542006) is greatly acknowledged.

Further Information

Publication History

Received: 04 December 2017

Accepted after revision: 16 January 2018

Publication Date:
21 February 2018 (online)

    Permissions and Reprints All articles of this category


Abstract

An intramolecular cyclization of various α-acyl β-amino acrylamides in the presence of PIFA and TFA is described. This transformation features mild reaction conditions, simple execution, high chemo­selectivity, and metal catalyst-free oxidation, and thereby, provides not only an alternative protocol for the construction of N–O bond, but also an efficient and straightforward synthesis of substituted isoxazol-3(2H)-ones from readily available α-acyl acrylamides.

Key words

acrylamides - cyclization - heterocycles - hypervalent iodine reagents - N–O bond formation - isoxazol-3(2H)-ones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609318.
  • Supporting Information