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Issue 73, 2012
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A cascade reaction of azolopyrimidines. Synthesis of unusual indole and azaindole derivatives

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Abstract

The reaction of bromo substituted pyrido[3′,2′:4,5]pyrrolo-[1,2-c]pyrimidine and pyrimido[1,6-a]indole methyl carboxylates with primary amines is described. The expected amide formation occurs but it is followed by an unexpected cascade process involving attack of the amine to the pyrimidine ring, opening of the pyrimidine ring, loss of the bromine substituent and competitive cyclizations to afford unusual imidazolidene substituted indoles and azaindoles.

Graphical abstract: A cascade reaction of azolopyrimidines. Synthesis of unusual indole and azaindole derivatives

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Publication details

The article was received on 25 Jun 2012, accepted on 20 Jul 2012 and first published on 23 Jul 2012


Article type: Communication
DOI: 10.1039/C2CC34539K
Citation: Chem. Commun., 2012,48, 9171-9173
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    A cascade reaction of azolopyrimidines. Synthesis of unusual indole and azaindole derivatives

    M. Morón, C. Burgos, J. Alvarez-Builla, A. Salgado, M. E. G. Mosquera and J. J. Vaquero, Chem. Commun., 2012, 48, 9171
    DOI: 10.1039/C2CC34539K

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