Synthesis 2016; 48(20): 3527-3536
DOI: 10.1055/s-0035-1562433
paper
© Georg Thieme Verlag Stuttgart · New York

A One-Pot, Multicomponent Synthesis of Trifluoromethylated Spiropiperidines under Catalyst-Free Conditions

Wei Shi
a  Department of Chemistry, School of Science, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China
,
Yang Wang
a  Department of Chemistry, School of Science, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China
,
Yingjun Zhu
a  Department of Chemistry, School of Science, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China
,
Min Zhang
a  Department of Chemistry, School of Science, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China
,
Liping Song*
a  Department of Chemistry, School of Science, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China
b  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
,
Hongmei Deng
c  Laboratory for Microstructures, Shanghai University, Shanghai, 200444, P. R. of China   Email: lpsong@shu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 11 March 2016

Accepted after revision: 03 May 2016

Publication Date:
28 June 2016 (online)


Abstract

A convenient, efficient, one-pot strategy for the synthesis of structurally diverse trifluoromethylated spirotetrahydropyridine-3-carboxylate derivatives is disclosed by taking advantage of a four-component reaction involving arylidene isoxazol-5-ones, aromatic aldehydes, ethyl 4,4,4-trifluoro-3-oxobutanoate and ammonium acetate. Additionally, a more consecutive approach to the same products is achieved via a one-pot, multicomponent reaction. The protocol allows easy access to trifluoromethylated spiroheterocycles in moderate to good yields under mild and catalyst-free conditions.

Supporting Information

 
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