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Chemo- and Regioselective 1,3-Dipolar Cycloaddition of Nitrile Imines to 5-Arylmethylene-2-methylthiohydantoinsстатья
Информация о цитировании статьи получена из
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 15 апреля 2026 г.
- Авторы: Filkina Maria E., Lintsov Lev A., Tafeenko Victor A., Kukushkin Maxim E., Beloglazkina Elena K.
- Журнал: Organics
- Том: 7
- Номер: 1
- Год издания: 2026
- Издательство: MDPI
- Местоположение издательства: Basel, Switzerland
- Номер статьи: 7
- DOI: 10.3390/org7010007
- Аннотация: 1,3-Dipolar cycloaddition reactions of nitrile imines are a powerful tool for the construction of spirocyclic frameworks, yet controlling chemoselectivity remains challenging when dipolarophiles contain multiple reactive sites. In this study, we investigated the cycloaddition of nitrile imines with 5-arylmethylene-2-methylthiohydantoins, which possess both exocyclic C=C and endocyclic C=N bonds. Nitrile imines were generated from hydrazonoyl chlorides under basic conditions and reacted with the thiohydantoin substrates under optimized reaction conditions. The cycloaddition proceeded smoothly, affording spiro-fused thiohydantoin–pyrazoline derivatives. In all cases, the reaction occurred selectively at the exocyclic C=C bond, while the C=N bond remained unreactive even in the presence of excess dipole. This chemoselectivity is attributed to the greater steric accessibility of the exocyclic double bond. These results clarify key factors governing nitrile imine chemoselectivity and provide a reliable approach to structurally complex spirocyclic thiohydantoin derivatives.
- Добавил в систему: Белоглазкина Елена Кимовна
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