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Issue 38, 2017
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Selective synthesis of tetrahydroimidazo[1,2-a]pyridine and pyrrolidine derivatives via a one-pot two-step reaction

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Abstract

In the presence of triethylamine, the addition reaction of substituted α-amino acid alkyl esters including ethyl hyperphenylalaninate, phenylalaninate, isoleucinate, and alaninate with dialkyl but-2-ynedioate afforded active β-enamino esters, which in turn reacted with aromatic aldehydes and malononitrile to give tetrahydroimidazo[1,2-a]pyridine derivatives in moderate yields. Under similar reaction conditions, the reaction of ethyl glycinate with dialkyl but-2-ynedioate resulted in a 1,3-dipolar azomethine ylide, which reacted further with in situ-generated arylidene malononitrile, alkyl cyanoacetate, and cyanoacetamide to give polysubstituted pyrrolidine derivatives in good yields.

Graphical abstract: Selective synthesis of tetrahydroimidazo[1,2-a]pyridine and pyrrolidine derivatives via a one-pot two-step reaction

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Publication details

The article was received on 27 Jul 2017, accepted on 18 Aug 2017 and first published on 18 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01860F
Citation: Org. Biomol. Chem., 2017,15, 8072-8077
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    Selective synthesis of tetrahydroimidazo[1,2-a]pyridine and pyrrolidine derivatives via a one-pot two-step reaction

    Y. Zhang, J. Sun, G. Shen and C. Yan, Org. Biomol. Chem., 2017, 15, 8072
    DOI: 10.1039/C7OB01860F

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