Microwave-Assisted Paal-Knorr Reaction - Three-Step Regiocontrolled Synthesis of Polysubstituted Furans, Pyrroles and Thiophenes

Giacomo Minetto, Luca F. Raveglia, Alessandro Sega, Maurizio Taddei*

*Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro, 53100 Siena, Italy, Email: taddei.munisi.it

G. Minetto, L. F. Raveglia, A. Sega, M. Taddei, Eur. J. Org. Chem., 2005, 5277-5288.

DOI: 10.1002/ejoc.200500387

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Abstract

An efficient and highly versatile microwave-assisted Paal-Knorr condensation of various 1,4-diketones gave furans, pyrroles and thiophenes in good yields. In addition, transformations of the methoxycarbonyl moiety, such as Curtius rearrangement, hydrolysis to carboxylic acid, or the conversion into amine by reaction with a primary amine in the presence of Me₃Al, are described.

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Key Words

Pyrroles, Furans, Thiophenes, Paal-Knorr (Furan, Pyrrole, Thiophene) Synthesis, Microwaves, Microwave Synthesis, Cyclocondensation, Peptidomimetics, Lawesson's Reagent

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ID: J24-Y2005-2220