Chemistry of thienopyridines. XXXIII. Synthetic routes to 5??and 7??substituted thieno [3, 2??b] pyridines from the N??oxide

LH Klemm, JN Louris, W Boisvert…

Index: Klemm, L. H.; Louris, John N.; Boisvert, William; Higgins, Clay; Muchiri, Daniel R. Journal of Heterocyclic Chemistry, 1985 , vol. 22, p. 1249 - 1252

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Citation Number: 10

Abstract

Abstract Thieno [3, 2-b] pyridine (1) is oxidized to N-oxide 1a by means of m- chloroperoxybenzoic acid (83%). Compound 1a forms adducts with hydrogen chloride and picric acid and gives ring substitution alpha or gamma to the heteronitrogen atom. Thus, 1a plus nitric and sulfuric acids produces the 7-nitro-N-oxide 1m (63%), or plus phosphorus oxychloride gives a mixture of 5-chloro and 7-chloro (1j) derivatives of 1. Compound 1m is ...