Functionalization of 2-methyl-and 2, 7-dimethyl-1, 8-naphthyridine

GR Newkome, KJ Theriot, VK Majestic…

Index: Newkome, George R.; Theriot, Kevin J.; Majestic, Veronica K.; Spruell, Perri Anne; Baker, Gregory R. Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2838 - 2842

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Citation Number: 12

Abstract

A new synthesis of 2, 7-dimethyl-l&naphthyridine (dmnap) from P-methyl-l, 8-naphthyridine (mnap) upon treatment with 3 equiv of methyllithium is described. Oxidation of dmnap with 8 equiv of N-chlorosuccinimide gave (98%) 2, 7-bis (trichloromethyl)-l, 8-naphthyridine (2), while oxidation with 4 equiv gave (97%) 2, 7-bis-(dichloromethy1)-l&naphthyridine (1). Hydrolysis of 2 with phosphoric acid followed by esterification gave the corresponding ...