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Synthesis of quinazoline-3-oxides via a Pd(II) catalyzed azide–isocyanide coupling/cyclocondensation reaction

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Abstract

A novel and efficient protocol concerning palladium catalyzing the three-component reaction of 2-azidobenzaldehyde, isocyanide, and hydroxylamine hydrochloride is developed. This method allows the rapid elaboration of quinazoline 3-oxides in a one-pot fashion. The 3-CR mainly involves concatenation of azide–isocyanide denitrogenative coupling, condensation with hydroxylamine and 6-exo-dig cyclization. The salient features of the methodology are operational simplicity, use of milder reaction conditions, being devoid of any additives such as oxidants (redox neutral) or base, and releasing N2 and H2O as the byproducts.

Graphical abstract: Synthesis of quinazoline-3-oxides via a Pd(ii) catalyzed azide–isocyanide coupling/cyclocondensation reaction

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Publication details

The article was received on 23 Oct 2018, accepted on 03 Dec 2018 and first published on 03 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02627K
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Synthesis of quinazoline-3-oxides via a Pd(II) catalyzed azide–isocyanide coupling/cyclocondensation reaction

    R. S. Pathare, A. K. Maurya, A. Kumari, V. K. Agnihotri, V. P. Verma and D. M. Sawant, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02627K

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