Straightforward and Efficient Protocol for the Synthesis of Pyrazolo [4,3-b]pyridines and Indazoles Научная публикация
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International Journal of Molecular Sciences
ISSN: 1661-6596 , E-ISSN: 1422-0067 |
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| Вых. Данные | Год: 2023, Том: 24, Номер: 2, Номер статьи : 1758, Страниц : DOI: 10.3390/ijms24021758 | ||
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Реферат:
An efficient method for the synthesis of pyrazolo [4,3-b]pyridines has been developed on the basis of readily available 2-chloro-3-nitropyridines via a sequence of SNAr and modified Japp–Klingemann reactions. The method offers a number of advantages including utilization of stable arenediazonium tosylates, operational simplicity as well as combining the azo-coupling, deacylation and pyrazole ring annulation steps in a one-pot manner. An unusual rearrangement (C-N-migration of the acetyl group) was observed and a plausible mechanism was proposed based on the isolated intermediates and NMR experiments. In addition, the developed protocol was successfully applied to the synthesis of 1-arylindazoles combining the Japp–Klingemann reaction and cyclization of the resulting hydrazone as a one-pot procedure.
Библиографическая ссылка:
Nikol’skiy V.V.
, Minyaev M.E.
, Bastrakov M.A.
, Starosotnikov A.M.
Straightforward and Efficient Protocol for the Synthesis of Pyrazolo [4,3-b]pyridines and Indazoles
International Journal of Molecular Sciences. 2023. V.24. N2. 1758 . DOI: 10.3390/ijms24021758 WOS Scopus OpenAlex
Straightforward and Efficient Protocol for the Synthesis of Pyrazolo [4,3-b]pyridines and Indazoles
International Journal of Molecular Sciences. 2023. V.24. N2. 1758 . DOI: 10.3390/ijms24021758 WOS Scopus OpenAlex
Идентификаторы БД:
| Web of science: | WOS:000915416900001 |
| Scopus: | 2-s2.0-85146579529 |
| OpenAlex: | W4316466286 |