Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates Научная публикация
| Журнал |
Molecules
, E-ISSN: 1420-3049 |
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| Вых. Данные | Год: 2022, Том: 27, Номер: 22, Страницы: 7913 Страниц : 1 DOI: 10.3390/molecules27227913 | ||||
| Ключевые слова | alkynes; cycloaddition; heterocycles; oxidation; iron | ||||
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Реферат:
A series of pyrazolo[1,5-a]pyridine-3-ylphosphonates were prepared with moderate to good yields by the oxidative [3+2]cycloaddition of 2-subtituted ethynylphosphonates with in situ generated pyridinium-N-imines and their annulated analogs. 2-Aliphatic and 2-Ph acetylenes demonstrate low activity, and the corresponding pyrazolopyridines were achieved with a moderate yield in the presence of 10 mol% Fe(NO3)3·9H2O. At the same time, tetraethyl ethynylbisphosphonate, diethyl 2-TMS- and 2-OPh-ethynylphosphonates possess much greater reactivity and the corresponding pyrazolo[1,5-a]pyridines, and their annulated derivatives were obtained with good to excellent yields without any catalyst. 2-Halogenated ethynylphosphonates also readily reacted with pyridinium-N-imines, forming complex mixtures containing poor amounts of 2-halogenated pyrazolopyridines.
Библиографическая ссылка:
Philippov I.
, Gatilov Y.
, Sonina A.
, Vorob’ev A.
Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates
Molecules. 2022. V.27. N22. P.7913. DOI: 10.3390/molecules27227913 WOS РИНЦ OpenAlex
Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates
Molecules. 2022. V.27. N22. P.7913. DOI: 10.3390/molecules27227913 WOS РИНЦ OpenAlex
Даты:
| Поступила в редакцию: | 20 окт. 2022 г. |
| Принята к публикации: | 4 нояб. 2022 г. |
| Опубликована online: | 16 нояб. 2022 г. |
Идентификаторы БД:
| Web of science: | WOS:000887304000001 |
| РИНЦ: | 57651109 |
| OpenAlex: | W4309604975 |