Tetrahedron

α-(3-Pyridyl) malonates: preparation and synthetic applications

F Tjosås, NM Pettersen, A Fiksdahl

Index: Tjosas, Freddy; Pettersen, Nina Marie; Fiksdahl, Anne Tetrahedron, 2007 , vol. 63, # 48 p. 11893 - 11901

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Citation Number: 6

Abstract

Alkylation of aromatic rings is a major challenge in organic syntheses since more complex carbon skeletons can be constructed. The alkylation of pyridine by nucleophilic aromatic substitution of the nitro group in methyl 3-nitro-4-pyridylcarboxylate (1) with malonic ester is reported. The versatility of the α-(3-pyridyl) malonic ester product (3) is demonstrated by the formation of a number of new 3-alkylated pyridines and new fused bis-heterocycles. cis 2- ...