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Issue 8, 2018
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An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction

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Abstract

A concise and efficient one-pot synthesis of novel N-fused tricyclic derivatives has been developed by using the Groebke–Blackburn–Bienaymé (GBB) reaction, which involved the reaction of 3-amino-1H-indazoles, aldehydes and isonitriles to afford 2-aryl-5H-imidazo[1,2-b]indazol-3-amine derivatives via a formal [4 + 1] cycloaddition reaction. Furthermore, we describe an unprecedented reaction of chromone-3-carboxaldehydes with 3-amino-1H-indazoles to afford (2-hydroxyphenyl)(pyrimido[1,2-b]indazol-3-yl)methanones in one-pot at ambient temperature. This protocol features a robust method for the one-step construction of new tricyclic rings, column chromatography free methods with a clean reaction profile, high yields, operational simplicity and it tolerates a diverse collection of reactants.

Graphical abstract: An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction

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Publication details

The article was received on 28 Nov 2017, accepted on 22 Jan 2018 and first published on 22 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02933K
Citation: Org. Biomol. Chem., 2018,16, 1287-1296
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    An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction

    S. G. Balwe and Y. T. Jeong, Org. Biomol. Chem., 2018, 16, 1287
    DOI: 10.1039/C7OB02933K

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