Issue 2, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 oct. 2018
Accepted
03 déc. 2018
First published
03 déc. 2018

Org. Biomol. Chem., 2019,17, 363-368

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, 17, 363 DOI: 10.1039/C8OB02627K

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