Antol, Ivana; Štrbac, Petar; Murata, Yasujiro; Margetić, Davor (2024) 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. International Journal of Molecular Sciences, 25 (12). ISSN 1422-0067
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Abstract
The reaction mechanism of the 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.
| Item Type: | Article | ||||||||
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| Uncontrolled Keywords: | 1,3-dipolar cycloadditions; DFT calculations; isatine; azomethine ylide; reaction mechanism | ||||||||
| Subjects: | NATURAL SCIENCES > Chemistry | ||||||||
| Divisions: | Division of Organic Chemistry and Biochemistry | ||||||||
| Projects: |
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| Depositing User: | Ivana Vuglec | ||||||||
| Date Deposited: | 13 Oct 2025 08:39 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/9997 | ||||||||
| DOI: | 10.3390/ijms25126524 |
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