FUROPYRIDINES .18. PHOTOCYCLOADDITION OF FURO[2,3-C]PYRIDIN-7(6H)-ONEWITH ACRYLONITRILE

The photocycloaddition of furo[2,3-c]pyridin-7(6H)-one (1) and its N-m ethyl derivative (1-Me) to acrylonitrile has been studied. The structu res of the photoadducts isolated by colum chromatography were determin ed by the nuclear magnetic resonance spectroscopy and single crystal X -ray analysis. The cyclo-addition of 1 afforded an adduct 2 at the car bonyl oxygen and 8-cyano-8,9-dihydrofuro[d]azocin-7(6H)-one (3), and t he addition of 1-Me the N-methyl derivative 3-Me of 3, ano-6-methyl-3a ,7a-dihydro-3a,7a-ethanofuro[2,3-c] pyridin-7(6H)-one (4), (2S, 2aR* 7bR)-(5) and (1R*, 2aS*, 3-methyl-4-oxo-1,2,2a,3,4,7b-hexahydrocyclob uta[e] furo[2,3-c]pyridine (6).