Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Oxidative and Thermal Routes to Novel Isoxazolopyridines

LK Dyall, DW Maloney, JJ Harvey and BE Fulloon

Australian Journal of Chemistry 49(7) 761 - 765
Published: 1996


The novel bicyclic compounds isoxazolo [3,4-b] pyridine (1). 3-phenylisoxazolo [3,4- b] pyridine (2) and 3-phenylisoxazolo[3,4-c]pyridine (3) have been synthesized by oxidative cyclization of the amines 2-aminopyridine-3-carbaldehyde (4), (2-amino-3-pyridyl)phenylmethanone (5) and (3-amino-4-pyridyl)phenylmethanone (6). The oxidant was bis(acetato-O)phenyliodine. 3-Phenylisoxazolo[3,4-c]pyridine (3) was also obtained by thermolysis of 3-azido-4-benzoylpyridine (7). Comparison of the rate of thermolysis of this azide with that of 3-azidopyridine identified a neighbouring group effect (from the benzoyl group) which is about four times as large as in a corresponding 2-azidobenzophenone. COSY and HETCOR techniques have been used to assign the 1H and 13C n.m.r. spectra of isoxazolo[3,4-b]pyridine (1).

© CSIRO 1996

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