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The three-component reaction of 2-hydroxy-1,4-naphthaquinone, aldehydes, and 6-aminouracil derivatives in acetic acid/water (1 : 1; v/v) under microwave heating conditions provides 1,4-dihydropyridines fused with naphthaquinone and pyrimidines. On the other hand the same reaction combinations under conventional reflux conditions provide acyclic trisubstituted methane derivatives. Using these tuneable reaction conditions a series of polycyclic fused N-heterocycles has been synthesized. The notable features of this methodology are a simple metal-free one-pot operation, easy purification process, use of the green solvent water, short reaction time and good to moderate yields of the products.

rsc advances

Molecular diversity from the three-component reaction of 2-hydroxy-1,4-naphthaquinone, aldehydes and 6-aminouracils: a reaction condition dependent MCR