Tetrahedron

Microwave-assisted synthesis of pyridylpyrroles from N-acylated amino acids

K Harju, N Manevski, J Yli-Kauhaluoma

Index: Harju, Kirsi; Manevski, Nenad; Yli-Kauhaluoma, Jari Tetrahedron, 2009 , vol. 65, # 47 p. 9702 - 9706

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Citation Number: 16

Abstract

A small library of 3-and 4-pyridyl-substituted pyrroles was prepared from N-acylated amino acids. Nicotinoyl or isonicotinoyl chloride was used for the N-acylation of benzyl esters of amino acids. Debenzylation by palladium-catalyzed hydrogenation gave N-acylated amino acids. Dehydration of the acylated amino acids gave cyclic intermediates, münchnones or azlactones, which were treated in situ with alkynes in 1, 3-dipolar cycloadditions. The ...