Pyrazolopyridines. The Preparation of 1-Protected-1H-pyrazolopyridines and Attempts to Remove the 1-Substituent. Some Reactions of 1-Benzyl-1H-pyrazolopyridine and its 7-Oxide

DOI: 10.1039/P19800000938

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 938 - 942 (1980)

Update date:2022-08-05

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Authors:

Dorgan, Roderick J.J.

Parrick, John

Hardy, Christopher R.

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Article abstract of DOI:10.1039/P19800000938

1-Protected-1H-pyrazolo<3,4-b>pyridines and -1H-pyrazolo<3,4-b>pyridin-6(7H)-ones have been obtained from 1-substituted-5-aminopyrazoles , and the removal of the protecting groups has been investigated.Cyclisation of 1-substituted-5-aminopyrazoles with ethyl acetoacetate under acidic conditions or of the β-aminopropionic acid derivative (19) under the same conditions gave only the 1H-pyrazolo<3,4-b>pyridin-6(7H)-one isomer .N-Oxidation of 1-benzyl-1H-pyrazolo<3,4-b>pyridine (4) gave the 7-oxide (21) which yielded (20) and the less usual β-substitution product (22) with acetic anhydride.Nitration of either (4) or (21) gave only substitution at the para-position of the 1-benzyl substituent, but bromination or chlorination gave substitution at the 3-position of the heterocycle.

Full text of DOI:10.1039/P19800000938

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