Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 31, Pages 5227-5233Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601024
Keywords
Nitrogen heterocycles; Heterogeneous catalysis; Copper; Manganese; Cyclization
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Funding
- Department of Science and Technology (DST)
- DST - Science and Engineering Research Board (SERB) under the Fast-Track Scheme [SR/FT/CS-168/2011]
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A new method for the synthesis of 2-arylquinazolin-4-(3H)-ones that involves a three-component coupling reaction of 2-bromobenzamide, aryl aldehydes, and aqueous ammonia has been developed. This protocol employs Cu-Mn spinel oxide as a heterogeneous catalyst and does not require the presence of a ligand or external oxidant. Key features of the reaction include a recyclable catalyst, ligand-free conditions, and a wide scope of possible substrates. The mechanism begins with the replacement of the bromine atom with NH2 from aqueous ammonia followed by imine formation, intramolecular ring cyclization (C-N bond formation), and aromatization.
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