Efficient Synthesis of 4,7-Dihydro-1H-oxepino[2,3-c]pyrazoles by Potassium Carbonate Promoted [4+3] Annulation of Crotonate-Derived Sulfur Ylides with Benzylidenepyrazolones

Dian Wang; Xue Wang; Xuange Zhang; Zhiwei Miao

doi:10.1055/s-0037-1610693

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(10): 2149-2156
DOI: 10.1055/s-0037-1610693

paper

Efficient Synthesis of 4,7-Dihydro-1H-oxepino[2,3-c]pyrazoles by Potassium Carbonate Promoted [4+3] Annulation of Crotonate-Derived Sulfur Ylides with Benzylidenepyrazolones

Dian Wang

^aState Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: miaozhiwei@nankai.edu.cn

,

Xue Wang

^aState Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: miaozhiwei@nankai.edu.cn

,

Xuange Zhang

^aState Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: miaozhiwei@nankai.edu.cn

,

Zhiwei Miao *

^aState Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: miaozhiwei@nankai.edu.cn

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China

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Abstract

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Dedicated in celebration of the 100^th anniversary of Nankai University

Abstract

The [4+3] annulation reaction of crotonate-derived sulfur ylides with benzylidenepyrazolones using K₂CO₃ as the base is reported. The ready availability of starting materials and the simple cyclization procedure make this approach suitable for the preparation of a diverse array of 4,7-dihydro-1H-oxepino[2,3-c]pyrazoles in good to excellent yields.

Key words

4,7-dihydro-1H-oxepino[2,3-c]pyrazoles - [4+3] annulation reaction - crotonate-derived sulfur ylides - benzylidenepyrazolones - reaction mechanism

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Referenzen

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