Synthesis

ortho-Hydroxyalkylation of Aminopyridines: A Novel Approach to Heterocycles

P Zakrzewski, M Gowan, LA Trimble, CK Lau

Index: Zakrzewski, Peter; Gowan, Mathew; Trimble, Laird A.; Lau, Cheuk K. Synthesis, 1999 , # 11 p. 1893 - 1902

Full Text: HTML

Citation Number: 2

Abstract

Abstract: Reaction of 6-substituted N-alkyl-3-aminopyridines with aldehydes in the presence of dichlorophenylborane gives selectively 2-hydroxyalkyl-3-aminopyridines. Dehydration of the latter under pyrolytic or Lewis acid conditions generates a quinone methide imine intermediate which can undergo electrocyclic or [4+ 2] cycloaddition reactions to give naphthyridines, dihydronaphthyridines or tetrahydronaphthyridines. Palladium-catalyzed ...