Molecular Diversity 2015-01-01

Ionic liquid-supported synthesis of dihydroquinazolines and tetrahydroquinazolines under microwave irradiation.

Jonathon Hull, Vinood Patel, Maya El Hindy, Christopher Lee, Esther Odeleye, Mohammed Hezwani, Seth Love, Patrick Kehoe, Katy Chalmers, Myra Conway

Index: Mol. Divers. 16(2) , 241-9, (2012)

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Abstract

An efficient microwave-assisted and water-soluble ionic liquid (IL)-supported synthesis of medicinally important dihydro- and tetrahydroquinazolines has been developed. The protocol involves the S(N)2 substitution reaction of IL-bound 4-bromomethyl-3-nitrobenzoic acid with various primary amines to provide IL-bound 4-((alkylamino) methyl)-3-nitrobenzoate under microwave irradiation. Further elaboration followed by sequential cyclization with various isothiocyanates and aldehydes furnished IL-bound target compounds. Cleavage of the IL support by methanolysis gave dihydro- and tetrahydroquinazolines with high purity and excellent yields. The new protocol has the advantages of shorter reaction time, easy workup process, excellent yields, reduced environmental impact, wide substrate scope, and convenient procedure.