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Transformation of 4-oxo-4H-[1]-benzopyran-3-carboxaldehydes into pyrazolo[3,4-B]pyridines

✍ Scribed by Henrieta Stankovičová; Anton Gáplovský; Margita Lácová; Jarmila Chovancová; Agnieszka Puchala

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 317 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430405

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✦ Synopsis

Abstract

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Reaction of 6‐methyl‐4‐oxo‐4__H__‐[1]‐benzopyran‐3‐carboxaldehyde 1 with 5‐amino‐3‐methyl‐1‐phenylpyrazole 2 in alcoholic reaction media in the presence of 4‐toluenesulfonic acid as catalyst afforded 5‐(2‐hydroxy‐5‐methylbenzoyl)‐3‐methyl‐1‐phenyl‐1__H__‐pyrazolo[3,4‐b]pyridine 3 and 2‐methoxy‐6‐methyl‐3‐(3‐methyl‐1‐phenylpyrazol‐5‐ylaminomethylene)chroman‐4‐one 7. We explain the mechanism of formation of both products on the basis of kinetic study of individual reaction steps.

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