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Synthesis 2013; 45(3): 375-381
DOI: 10.1055/s-0032-1316836
paper
© Georg Thieme Verlag Stuttgart · New York

Three-Component Condensation for the Construction of Novel Spirooxindoles

Fei Ji
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
,
Mu Sun
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
,
Mei-fang Lv
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
,
Wen-bin Yi
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
,
Chun Cai*
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 13 November 2012

Accepted after revision: 05 December 2012

Publication Date:
21 December 2012 (online)

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Abstract

A new route for the synthesis of novel spirooxindoles from isocyanides, dialkyl acetylenedicarboxylates, and N-substituted isatylidene derivatives through [3+2] cycloaddition has been developed. This method has several advantages, such as high regioselectivity, high yields, readily available starting materials, and one-pot operations. The synthetic alkyne-containing spirooxindoles could also be used in the selective synthesis of triazole-containing­ spirocyclic compounds using a copper azide–alkyne cycloaddition­ (CuAAC) reaction.

Key words

multicomponent reaction - spirooxindoles - [3+2] cycloaddition - CuAAC reaction - triazoles

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information

Primary Data

    for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0036th
  • Primary Data
 

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