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Synthesis 2014; 46(04): 510-514
DOI: 10.1055/s-0033-1340470
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3,4,5-Trisubstituted Isoxazoles by the 1,3-Dipolar Cycloaddition Reaction of α-Azido Acrylates and Aromatic Oximes

Manman Hu
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
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Xinwei He
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
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Zhiqiang Niu
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
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Zhenglei Yan
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
,
Fuyin Zhou
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
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Yongjia Shang*
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
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Publication History

Received: 23 October 2013

Accepted after revision: 25 November 2013

Publication Date:
02 January 2014 (online)

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Abstract

A novel, one-pot, cascade reaction sequence featuring the 1,3-dipolar cycloaddition reaction of α-azido acrylates and aromatic oximes was developed. This procedure provides an efficient, straightforward and metal-free method for the synthesis of 3,4,5-trisubstituted isoxazoles under mild reaction conditions.

Key words

1,3-dipolar cycloaddition - α-azido acrylates - aromatic oximes - isoxazoles - one-pot synthesis

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