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Article

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 †

by
Ivana Antol
1,*,
Petar Štrbac
1,
Yasujiro Murata
2 and
Davor Margetić
1,*
1
Laboratory for Physical Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička Cesta 54, HR-10002 Zagreb, Croatia
2
Structural Organic Chemistry Laboratory, Division of Synthetic Chemistry, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
*
Authors to whom correspondence should be addressed.
†
Dedicated to Professor Ronald N. Warrener on the occasion of his 90th birthday.
Int. J. Mol. Sci. 2024, 25(12), 6524; https://doi.org/10.3390/ijms25126524
Submission received: 25 May 2024 / Revised: 7 June 2024 / Accepted: 10 June 2024 / Published: 13 June 2024
(This article belongs to the Special Issue Recent Progress in Addition Reactions and Organic Synthesis)
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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.
Keywords: 1,3-dipolar cycloadditions; DFT calculations; isatine; azomethine ylide; reaction mechanism 1,3-dipolar cycloadditions; DFT calculations; isatine; azomethine ylide; reaction mechanism

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MDPI and ACS Style

Antol, I.; Štrbac, P.; Murata, Y.; Margetić, D. 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. Int. J. Mol. Sci. 2024, 25, 6524. https://doi.org/10.3390/ijms25126524

AMA Style

Antol I, Štrbac P, Murata Y, Margetić D. 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. 2024; 25(12):6524. https://doi.org/10.3390/ijms25126524

Chicago/Turabian Style

Antol, Ivana, Petar Štrbac, Yasujiro Murata, and Davor Margetić. 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, no. 12: 6524. https://doi.org/10.3390/ijms25126524

APA Style

Antol, I., Štrbac, P., Murata, Y., & Margetić, D. (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), 6524. https://doi.org/10.3390/ijms25126524

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