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A new rapid multicomponent domino heteroannulation of heterocyclic ketene aminals: solvent-free regioselective synthesis of functionalized benzo[g]imidazo[1,2-a]quinolinediones
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China
E-mail: liming928@qust.edu.cn
Org. Biomol. Chem., 2013,11, 781-786
DOI:
10.1039/C2OB27137K
Received
02 Aug 2012,
Accepted
08 Nov 2012
First published online
09 Nov 2012
A highly efficient and straightforward three-component cascade reaction was developed to synthesize benzo[g]imidazo[1,2-a]quinolinedione derivatives from heterocyclic ketene aminals (HKAs), aldehydes, and 2-hydroxy-1,4-naphthoquinone (HNQ) via Et3N-catalyzed tandem [3 + 2 + 1] annulation under solvent-free conditions. The reactions were very mild, convenient and highly regioselective to form new fused tetracyclic target molecules.