Multicomponent Synthesis of 4-Aryl-1,4-Dihydro-Oxochromeno[3,2-b] Oxoindeno[6,5-e]Pyridine

Abstract

One pot multi-component strategy has been developed for the synthesis of a small library of nineteen 4-aryl-1,4-dihydro-oxochromeno[3,2-b]oxoindeno[6,5-e]pyridine by the condensation of 4-aminocoumarin, aromatic aldehyde and indane-1,3-dione in acetic acid:ethylene glycol (5:1) in good yields along with the formation of di-(4-aminocoumarin-3-yl)arylmethane as by product in three cases. The use of microwave irradiation for the condensation of 4-aminocoumarin, aromatic aldehyde and indane-1,3-dione in acetic acid and ethylene glycol at 200 W and at 120 °C led to the selective formation of 4-aryl-1,4-dihydro-oxochromeno[3,2-b]oxoindeno[6,5-e] pyridine in excellent yields. Interestingly, the side product di-(4-aminocoumarin-3-yl)arylmethane could be converted exclusively to 4-(4'-nitrophenyl)-1,4-dihydro-di(oxochromeno[3,2-b:5,6-e])pyridine on microwave irradiation under identical condition.

Keywords:

• 4-Aryl-14-dihydro-oxochromeno[32-b] oxoindeno[65-e]pyridine
• 14-dihydropyridines (DHPs)
• microwave irradiation
• multicomponent reactions

Additional information

Funding

SKS thanks UGC for providing the startup grant (No.F.30109/2015 BSR).