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Regioselective Cycloaddition of Nitrile Imines to 5-Methylidene-3-phenyl-hydantoin: Synthesis and DFT Calculationsстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Filkina Maria E., Baray Daria N., Beloglazkina Elena K., Grishin Yuri K., Roznyatovsky Vitaly A., Kukushkin Maxim E.
- Журнал: International Journal of Molecular Sciences
- Том: 24
- Номер: 2
- Год издания: 2023
- Издательство: MDPI
- Местоположение издательства: Basel, Switzerland
- Номер статьи: 1289
- DOI: 10.3390/ijms24021289
- Аннотация: Nitrile imine cycloaddition to hydantoins containing an exocyclic C=C double bond hasbeen previously described in a very limited number of examples. In this work, regioselective synthesisof spiro-pyrazoline-imidazolidine-2,4-diones based on a 1,3-dipolar cycloaddition reaction of nitrileimines to 5-methylidene-3-phenyl-hydantoin have been proposed. It was found that, regardless ofthe nature of the aryl substituents at the terminal C and N atoms of the C-N-N fragment of nitrile imine (electron donor or electron acceptor), cycloaddition to the 5- methylidenhydantoin exocyclic C=C bond proceeds regioselectively, and the terminal nitrogen atom of the nitrile imine connects to the more sterically hindered carbon atom of the double bond, which leads to the formation of a 5-disubstituted pyrazoline ring. The observed cycloaddition regioselectivity was rationalized using DFT calculations of frontier molecular orbital interactions, global CDFT reactivity indices, and minimum energy paths.
- Добавил в систему: Белоглазкина Елена Кимовна