S. Shiotani et al., FUROPYRIDINES .18. PHOTOCYCLOADDITION OF FURO[2,3-C]PYRIDIN-7(6H)-ONEWITH ACRYLONITRILE, Journal of heterocyclic chemistry, 33(6), 1996, pp. 1967-1976
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).