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Issue 86, 2015
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Acid/base-controlled chemodivergent synthesis of two differently functionalized tetrahydroimidazo[1,2-a]pyridines

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Abstract

A new approach for the facile chemodivergent synthesis of tetrahydroimidazo[1,2-a]pyridines from β-ketothioamides, aldehydes and heterocyclic ketene aminals is described. In the presence of a base, an unprecedented ring-opening, tautomerization, recyclization cascade is observed and H2S eliminated tetrahydroimidazo[1,2-a]pyridines were formed in good yields. With catalytic amounts of acid, another type of different substituted tetrahydroimidazo[1,2-a]pyridines were obtained through dehydration.

Graphical abstract: Acid/base-controlled chemodivergent synthesis of two differently functionalized tetrahydroimidazo[1,2-a]pyridines

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Publication details

The article was received on 08 Jul 2015, accepted on 12 Aug 2015 and first published on 12 Aug 2015


Article type: Paper
DOI: 10.1039/C5RA13395E
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2015,5, 70429-70432
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    Acid/base-controlled chemodivergent synthesis of two differently functionalized tetrahydroimidazo[1,2-a]pyridines

    W. Guo, X. Xin, K. Zhao, L. Wen and M. Li, RSC Adv., 2015, 5, 70429
    DOI: 10.1039/C5RA13395E

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