複素環式化合物の合成研究 (第43報)

フラン誘導体の合成 その2 Furo[3,2-c]pyridine誘導体及びその関連化合物の合成

抄録

1-(3′-Methoxy-4′-benzyloxyphenyl)-3, 4-dihydrofuro[3, 2-c]pyridine possesses uterus contracting action about 1/50 of that of oxytocin but its debenzylated compound is devoid of such action. This seemed to suggest that the benzyloxy group bonded to the phenyl in 1-position is the effective group and a compound in which the benzyloxy and methoxy groups in the above compound had been exchanged, the dibenzyloxy compound, the reduction product of each compound, and the benzoyloxy compound, i.e. 1-(3′-benzyloxy-4′-methoxyphenyl)-, 1-(3′, 4′-dibenzyloxyphenyl)-, and 1-(3′-methoxy-4′-benzoyloxyphenyl)-3, 4-dihydrofururo [3, 2-c]-pyridine, and 1-(3′-benzyloxy-4′-methoxyphenyl)- and 1-(3′, 4′-dibenzyloxyphenyl)-1, 2, 3, 4-tetrahydrofuro[3, 2-c]pyridine, were prepared by the Bischler-Napieralski reaction of the corresponding acid amides followed by reduction with sodium borohydride. Further, in order to examine the effect of the substituent in 1-position, N-methyl-3-methoxy-4-benzyloxybenzylamine was synthesized.