Tetrahedron letters

Synthesis of 2-amino-3-hydroxy-4-substituted pyridines via regioselective metalation of 3-(1-ethylpropyl)-[1, 3] oxazolo [4, 5-b] pyridin-2 (3H)-one and application to …

RA Hartz, KK Nanda, CL Ingalls

Index: Hartz, Richard A.; Nanda, Kausik K.; Ingalls, Charles L. Tetrahedron Letters, 2005 , vol. 46, # 10 p. 1683 - 1686

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Citation Number: 4

Abstract

An efficient route to the preparation of 2-amino-3-hydroxy-4-substituted pyridines is described. The key step involves the regioselective metalation and subsequent alkylation of the [1, 3] oxazolo [4, 5-b] pyridin-2 (3H)-one ring system. Base hydrolysis provides access to a variety of 4-substituted pyridines. This chemistry is proved to be useful for the synthesis of corticotropin releasing factor1 receptor ligands.