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Paper | Special issue | Vol 88, No. 2, 2014, pp.1065-1077
Published online, 2nd August, 2013
DOI: 10.3987/COM-13-S(S)65
■ Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines

Jin-Peng Zhang, Wei Fan, Jie Ding, Bo Jiang,* Shu-Jiang Tu,* and Guigen Li

*School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Gree Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Jiangsu 221116, China

Abstract

Regioselective three-component reactions of aromatic aldehydes with indazol-5-amine and 2-hydroxy-1,4-naphthoquinone in HOAc under microwave irradiation have been developed. In this one-pot reaction, a series of new pyrazole-fused benzo[h]acridine derivatives with 1,2-diketone unit were synthesized with high chemical yields. The resulting pyrazole-fused acridines were employed to further react with aldehydes and ammonium acetate to give polycyclic oxazole-fused pyrazolo[3,4-j]acridines. The present green synthesis shows several advantages including operational simplicity and fast reaction rates, which makes it a useful and attractive process of library generation for drug discovery.