ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Pyrrolo[2 ,3 :4,5]furo[3,2-c]pyridine Derivatives Reactions in the Pyridine and Pyrrole Ring

M. Bencková, A. Krutošíková, J. Pullman, and N. Prónayová

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak University of Technology, SK-812 37 Bratislava

E-mail: krutosik@chelin.chtf.stuba.sk

Abstract: Methyl 1-methylpyrrolo[2',3':4,5]furo[3,2-c]pyridine-2-carboxylate was oxidized with m-chloroperbenzoic acid in dichloromethane to 2-methoxycarbony-1-methylpyrrolo[2',3':4,5]furo[3,2-c]pyridine-7-oxide. Treatment of this compound with benzoyl chloride and cyanide anion (Reissert-Henze reaction) was shown to produce the corresponding methyl 8-cyano-1-methylpyrrolo[2',3':4,5]furo[3,2-c]pyridine-2-carboxylate. Methyl 1H-pyrrolo[2',3':4,5]furo[3,2-c]pyridine-2-carboxylate was prepared by reduction of methyl 8-chloro-1H-pyrrolo[2',3':4,5]furo[3,2-c]pyridine-2-carboxylate with hydrazine and palladium on carbon. Both esters with hydrazine hydrate yielded the corresponding carbohydrazides, which by reaction with orthoesters afforded 4-substituted 2H-pyrido [3",4":4',5']furo[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazin-1-ones.

Full paper in Portable Document Format: 532a118.pdf

Chemical Papers 53 (2) 118–122 (1999)