S. Shiotani, Y. Tsukamoto, Yukiko Kawahara
Nov 1, 1996
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Journal
Journal of Heterocyclic Chemistry
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).