Furopyridines. XVIII. Photocycloaddition of furo[2,3‐c]pyridin‐7(6H)‐one with acrylonitrile

Abstract

The photocycloaddition of furo[2,3‐c]pyridin‐7(6H)‐one (1) and its N‐mefhyl derivative (1‐Me) to acrylonitrile has been studied. The structures of the photoadducts isolated by colum chromatography were determined by the nuclear magnetic resonance spectroscopy and single crystal X‐ray analysis. The cyclo‐addition of 1 afforded an adduct 2 at the carbonyl oxygen and 8‐cyano‐8,9‐dihydrofuro[d]azocin‐7(6H)‐one (3), and the addition of 1‐Me the N‐methyl derivative 3‐Me of 3, (9S*)‐9‐cyano‐6‐methyl‐3a,7a‐dihydro‐3a,7a‐ethanofuro[2,3‐c]pyridin‐7(6H)‐one (4), (2S*, 2aR*, 7bR*)‐ (5) and (1R*, 2aS*, 7bS*)‐2‐cyano‐3‐methyl‐4‐oxo‐1,2,2a,3,4,7b‐hexahydrocyclobuta[e]furo[2,3‐c]pyridine (6).