APPLICATION OF SUPER-BASIC MEDIA IN ACETYLENE CHEMISTRY
Keywords:
Acetylene, amines, anabazine, vinylation, superbasic environment, catalyst, solvent.Abstract
The role of the highly basic KOH-DMSO system in the vinylation of amines is shown. The catalytic vinylation of anabazine with acetylene at atmospheric pressure has been studied. It has been found that anabazine vinyl derivatives are synthesized by analogy.
References
Schmidt E. Y., Trofimov B. A. Acetylene in Organic Synthesis. From the Chaos of Small Molecules to Highly Organized
Structures. A Review //Doklady Chemistry. - Moscow: Pleiades Publishing, 2022. - Т. 505. - №. 1. - С. 127-145.
Trofimov B. A., Schmidt E. Yu. Acetylenes in the Superbase-Promoted Assembly of Carbocycles and Heterocycles Acc. Chem. Res. 2018, 51, 5, 1117-1130https://doi.org/10.1021/acs.accounts.7b00618
Trofimov B.A., Schmidt E.Yu. Reactions of acetylenes in super-basic media. Recent achievements // Russian Chemical Review. - 2014. - Т. 83. - №. 7. - С. 600.
Vitkovskaya N. M. et al. Quantum-chemical models of KOH (KOBut)/DMSO superbasic systems and mechanisms of base-promoted acetylene reactions //International Journal of Quantum Chemistry. - 2020. - Т. 120. - №. 9. - P. e26158.
Pradedova A. G., Kobychev V. B. Quantum Chemical Study of the Mechanism of (E, Z)-1, 3-Diphenyl-2-Aza-1, 3-Diene Stereoselective Formation from N-Benzyl-1-Phenylethane-1-Imine and Acetylene in the KO t-Bu/DMSO Superbasic Environment //Journal of Structural Chemistry. - 2023. - Т. 64. - №. 3. - С. 386-397.
Absalyamov D. Z. et al. Quantum-Chemical Insight into Self-Organization of Complex Molecules from Acetylene and Anilines Catalyzed by Superbase KOH/DMSO: One-Pot Cascade Assembly of 1, 3-Bis (arylamines) //Asian Journal of Organic Chemistry. - 2023. - Т. 12. - №. 4. - P. e202300042.
Matake R., Adachi Y., Matsubara H. Synthesis of vinyl ethers of alcohols using calcium carbide under superbasic catalytic conditions (KOH/DMSO) //Green Chemistry. - 2016. - Т. 18. - №. 9. - С. 2614-2618.
Shabalin D. A. et al. A. et al. Calcium Carbide as Acetylene Source in Cascade Assemblies of Hydroxypyrrolines and 3H-Pyrroles from Ketoximes //ChemistrySelect. - 2020. - Т. 5. - №. 11. - С. 3434-3437.
Mirkhamitova D., Kozinskaya L. Catalytic vinylation of heterocyclic amines // LAP Lambert Academic P ublishing , 2021. pp. 117. (Monograph).