Synthesis 2016; 48(02): 293-301
DOI: 10.1055/s-0035-1560803
paper
© Georg Thieme Verlag Stuttgart · New York

Tin-Mediated One-Pot Synthesis of α,α-Disubstituted Homoallylic Hydrazides from Ketones, Acylhydrazines and Allyl Bromide

Ailing Lu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: huangdf@nwnu.edu.cn
,
Danfeng Huang*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: huangdf@nwnu.edu.cn
,
Ke-Hu Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: huangdf@nwnu.edu.cn
,
Yingpeng Su
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: huangdf@nwnu.edu.cn
,
Junyan Ma
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: huangdf@nwnu.edu.cn
,
Yanli Xu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: huangdf@nwnu.edu.cn
,
Yulai Hu*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. of China   Email: huangdf@nwnu.edu.cn
b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 22 July 2015

Accepted after revision: 30 September 2015

Publication Date:
04 November 2015 (online)


Abstract

An efficient multicomponent one-pot reaction was developed for the synthesis of α,α-disubstituted homoallylic hydrazides by treating ketones, acylhydrazines and allyl bromide with tin powder in tetrahydrofuran under reflux. The reaction proceeds smoothly without any catalyst under mild conditions to give the corresponding products in high yields.

Supporting Information

 
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