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- Title
Regioselective Cycloaddition of Nitrile Imines to 5-Methylidene-3-phenyl-hydantoin: Synthesis and DFT Calculations.
- Authors
Filkina, Maria E.; Baray, Daria N.; Beloglazkina, Elena K.; Grishin, Yuri K.; Roznyatovsky, Vitaly A.; Kukushkin, Maxim E.
- Abstract
Nitrile imine cycloaddition to hydantoins containing an exocyclic C=C double bond has been previously described in a very limited number of examples. In this work, regioselective synthesis of spiro-pyrazoline-imidazolidine-2,4-diones based on a 1,3-dipolar cycloaddition reaction of nitrile imines to 5-methylidene-3-phenyl-hydantoin have been proposed. It was found that, regardless of the 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.
- Subjects
RING formation (Chemistry); NITRILIMINES; FRONTIER orbitals; ISOXAZOLIDINES; ELECTRON donors; DOUBLE bonds; ORBITAL interaction
- Publication
International Journal of Molecular Sciences, 2023, Vol 24, Issue 2, p1289
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms24021289