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- Title
Theoretical Study of the Mechanism of the Formation of Azomethine Ylide from Isatine and Sarcosine and Its Reactivity in 1,3-Dipolar Cycloaddition Reaction with 7-Oxabenzonorbornadiene †.
- Authors
Antol, Ivana; Štrbac, Petar; Murata, Yasujiro; Margetić, Davor
- Abstract
The reaction mechanism of tthe formation of azomethine ylides from isatins and sarcosine is addressed in the literature in a general manner. This computational study aims to explore the mechanistic steps for this reaction in detail and to assess the reactivity of formed ylide in a 1,3-dipolar cycloaddition reaction with 7-oxabenzonorbornadiene. For this purpose, density functional theory (DFT) calculations at the M06-2X(SMD,EtOH)/6-31G(d,p) level were employed. The results indicate that CO2 elimination is the rate-determining step, the activation barrier for 1,3-dipolar cycloaddition is lower, and the formed ylide will readily react with dipolarophiles. The substitution of isatine with electron-withdrawal groups slightly decreases the activation barrier for ylide formation.
- Subjects
SCHIFF bases; RING formation (Chemistry); YLIDES; DENSITY functional theory
- Publication
International Journal of Molecular Sciences, 2024, Vol 25, Issue 12, p6524
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms25126524