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Paper | Regular issue | Vol 34, No. 7, 1992, pp.1353-1364
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6021
Synthesis of 11H-Furo[3’,2’:7,8]benzopyrano[3,4-c]pyridin-11-one and 6,8-Dimethyl-10H-pyrano[2’,3’:4,5]benzofuro[3,2-c]pyridin-10-one (Pyridoangelicins)

Jacqueline Moron,* Christiane Huel, and Emile Bisagni

*URA 1387, CNRS, Institut Curie, Section de Biologie, Centre Universitaire, Bat. 110-112, 91405 Orsay, France

Abstract

11H-Furo[3’,2’:7,8]benzopyrano[3,4-c]pyridin-11-one (3) was synthesized from 1-benzyl-3-ethoxycarbonylpiperidin-4-one and 2,3-dihydro-4-hydroxybenzofuran (5) ba a von Pechmann reaction and subsequent aromatization of the hexahydro derivative (6). 6,8-Dimethyl-10H-pyrano[2’,3’:4,5]benzofuro[3,2-c]pyridin-10-one (4a) was obtained by dehydrogenation of the tetrahydro derivative (10b). This compound was prepared from piperidinone-O-(4,6-dimethylcoumarin-7-yl) oxime (9d) using acid catalyzed Fischer indole-like reaction. Are also reported and compared the results of the reactions of piperidinone-O-(coumarin-7-yl) oxime (9d) and the corresponding 5-methyl (9e) derivative, in which the rearrangement occurs at both the 8 and the 6 positions.