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Catalyst-free synthesis of isoindolin-1-imine derivatives via multi-component reaction in water medium

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Abstract

A catalyst-free, one-pot method has been developed for the synthesis of isoindolin-1-imine derivatives via cascade three-component condensation of 2-cyanobenzaldehyde, amine, and active methylene compound (1,3-dimethylbarbituric acid, Meldrum’s acid, 5,5-dimethylcyclohexane-1,3-dione, and 1,3-cyclohexanedione). The efficient and convenient reaction provides the corresponding products from various substrates at room temperature in aqueous medium with excellent yields (90–98 %) via easy purification. The straightforward procedure is a valid contribution to the methodology for the synthesis of isoindolin-1-imine derivatives.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (grants 30925040, 81102329, 81273397), the Chinese National Science & Technology Major Project “Key New Drug Creation and Manufacturing Program” (grants 2013ZX09508104, 2012ZX09301001-001, 2011ZX09307-002-03), and the Science Foundation of Shanghai (grant 12XD1405700).

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Authors and Affiliations

  1. Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Shanghai, 201203, People’s Republic of China

    Sida Shen, Yijia Chen, Min Lei & Lihong Hu

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  1. Sida Shen
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  2. Yijia Chen
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  3. Min Lei
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  4. Lihong Hu
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Correspondence to Min Lei or Lihong Hu.

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Shen, S., Chen, Y., Lei, M. et al. Catalyst-free synthesis of isoindolin-1-imine derivatives via multi-component reaction in water medium. Monatsh Chem 146, 1571–1580 (2015). https://doi.org/10.1007/s00706-015-1449-0

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  • DOI: https://doi.org/10.1007/s00706-015-1449-0

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