Synthesis of quinazoline-3-oxides via a Pd(ii) catalyzed azide–isocyanide coupling/cyclocondensation reaction
Organic & Biomolecular Chemistry(2019)
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 N-2 and H2O as the byproducts.
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Key words
coupling/cyclocondensation reaction,synthesis,azide–isocyanide
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