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Paper | Regular issue | Vol 57, No. 1, 2002, pp.55-71
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9363
Synthesis of Melatonin Analogues Derived from Furo[2,3-b]- and [2,3-c]pyridines by Use of a Palladium-Copper Catalyst System

Hervé Van de Poël, Gérald Guillaumet, and Marie-Claude Viaud-Massuard*

*Laboratoire de Chimie Organique, UFR des Sciences Pharmaceutiques, Université de Tours, 31 Avenue de Monge, 37200 Tours, France

Abstract

2,3,5-Substituted furo[2,3-b]pyridine was synthesised by palladium-catalyzed reaction of 5-bromo-2-hydroxy-3-iodopyridine and phenylacetylene with (Ph3P)2PdCl2, CuI in Et3N. A carbonylative cyclization of 5-hydroxy-2-methoxy-4-(2-phenylethynyl)pyridine with carbon monoxide in methanol with PdCl2, CuCl2 under basic conditions, has been accomplished to prepare methyl 2,5-substituted furo[2,3-c]pyridine-3-carboxylate.