Synthesis 2014; 46(18): 2422-2429
DOI: 10.1055/s-0034-1378660
feature article
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,3,5-Trisubstituted Pyrazoles by the Cope-Type Hydroamination of 1,3-Dialkynes with Alkylhydrazines

Xiaoqiang Yu*
a   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China   Fax: +86(411)84986180   eMail: yuxiaoqiang@dlut.edu.cn   eMail: mingbao@dlut.edu.cn
,
Nan Huang
a   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China   Fax: +86(411)84986180   eMail: yuxiaoqiang@dlut.edu.cn   eMail: mingbao@dlut.edu.cn
,
Xiujuan Feng
a   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China   Fax: +86(411)84986180   eMail: yuxiaoqiang@dlut.edu.cn   eMail: mingbao@dlut.edu.cn
,
Yoshinori Yamamoto
a   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China   Fax: +86(411)84986180   eMail: yuxiaoqiang@dlut.edu.cn   eMail: mingbao@dlut.edu.cn
b   WPI-AIMR (WPI-Advanced Institute for Materials Research), Tohoku University, Sendai 980-8577, Japan
,
Ming Bao*
a   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China   Fax: +86(411)84986180   eMail: yuxiaoqiang@dlut.edu.cn   eMail: mingbao@dlut.edu.cn
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Publikationsverlauf

Received: 30. Mai 2014

Accepted after revision: 04. Juli 2014

Publikationsdatum:
29. Juli 2014 (online)


Abstract

An efficient method to synthesize 1,3,5-trisubstituted pyrazoles was developed. The reaction of 1,3-dialkynes with alkylhydrazines smoothly proceeded in dimethyl sulfoxide under suitable heating conditions to produce 1,3,5-trisubstituted pyrazoles in satisfactory to excellent yields.

Supporting Information