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Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination

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Abstract

An efficient environmentally benign route for the synthesis of benzimidazo[2,1-a]isoquinoline has been developed by reacting 2-ethynylbenzaldehyde and related substituted alkynylbenzaldehydes with variously substituted ortho-phenylenediamines and aliphatic amines in ethanol. This method provides a convenient, room temperature, atom-economical, and catalyst-free access to diversely substituted isoquinoline fused benzimidazoles. Regioselectivity of the reaction, as referred to o-phenylenediamines, was confirmed by X-ray crystallography. The reaction was found to occur in three major steps (imine formations, cyclization, and aromatization) and a mechanism has been proposed.

Graphical abstract: Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination

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Publication details

The article was received on 09 Aug 2018, accepted on 12 Nov 2018 and first published on 12 Nov 2018


Article type: Paper
DOI: 10.1039/C8GC02520G
Citation: Green Chem., 2019, Advance Article
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    Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination

    M. Mishra, D. Twardy, C. Ellstrom, K. A. Wheeler, R. Dembinski and B. Török, Green Chem., 2019, Advance Article , DOI: 10.1039/C8GC02520G

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