Indium(III) Chloride: An Efficient Catalyst for One-Pot Multicomponent Synthesis of 2,3-dihydroquinazoline-4(1H)-ones

ISSN： 2213-3372

Source： Current Organocatalysis, Vol.5, Iss.2, 2018-05, pp. : 137-144

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Abstract

Background: Multicomponent reactions (MCRs) are one of the most revolutionary conceptsin synthetic organic chemistry. By definition, an MCR is a convergent chemical process involvingthree or more reactants to fabricate products which retain all structural and substructural features of thestarting materials. The value of MCRs lies in all areas of synthetic chemistry, as they offer shorter reactiontime, uncomplicated process protocol and high yield. We here reported a novel, effortless, ecofriendlymulti-component one-pot synthesis of potent 2,3-dihydroquinazoline-4(1H)-ones is disclosed.

Methods: The method causes condensation of isatoic anhydride, ammonium salts and aromatic aldehydesin ethanol. The reaction further employs metal chloride catalyst and offers significant advantagesincluding the use of green solvent and unsophisticated work-up methodology. Additionally,the method is of value owing to the excellent yield obtained by the reaction.

Results: The multicomponent reaction of isatoic anhydride and ammonium chloride with various aldehydeswas investigated in presence of ethanol at reflux for 1.5 h. The catalytic MCR of a substitutedaldehyde with ammonium chloride and isatoic anhydride generates 10 products with percentage yieldranging from 84-95%.

Conclusion: In a nutshell, it can be stated that indium chloride-catalyzed multi-component reaction isa novel and efficient method for the synthesis of 2,3-dihydroquinazoline-4(1H)-ones. Significant advantagesof the method include the use of simple and readily available precursors, high yield and easyworkup with short reaction times. Better reactivity of ammonium chloride and high catalytic activityof InCl3 is an added advantage while using ethanol as a green solvent renders the reaction an ecocompatiblestatus.