Three-Component Synthesis of Enaminones Based on Homoveratrilamine and Aromatic Aldehydes
Abstract
An efficient one-reactor procedure leading to β-enaminones has been developed. The developed methodology involves a multicomponent [1+2+1] cyclocondensation reaction of starting materials. As starting materials we used homoveratrilamine as the primary amine source and acetoacetic ether as the dicarbonyl compound and a number of aromatic aldehydes. Mild reaction conditions, simple and rapid methods of purification and separation of the obtained products further facilitated the synthesis process. The structure of the synthesized substances was established by IR, 1 H and 13C NMR spectra and physical constants were studied.
References
Sowmya PV et al. Novel 2-methyl-6-arylpyridines carrying active pharmacophore 4, 5-dihydro 2-pyrazolines: synthesis, antidepressant, and anti-tuberculosis evaluation // Research on Chemical Intermediates. – 2017. – v. 43. – P. 7399-7422.
Alexander MS et al. Enaminones 11. An examination of some ethyl ester enaminone derivatives as anticonvulsant agents //Bioorganic & medicinal chemistry. – 2013. – T. 21. – №. 11. – C. 3272-3279.
Afsah EM et al. Mannich Reaction with Enaminones: Convenient Synthesis of Functionalized Tetrahydro-pyrimidines, Dihydro-1, 3-oxazines, and Dihydro-1, 2, 4-triazepines // Journal of Heterocyclic Chemistry. – 2018. – T. 55. – №. 12. – C. 2959-2970.
Zhao Y. et al. Gold-catalyzed chemo-and diastereoselective C ( sp 2)–H functionalization of enaminones for the synthesis of pyrrolo [3, 4-c]-quinolin-1-one derivatives //Organic & Biomolecular Chemistry. – 2016. – T. 14. – №. 7. – C. 2177-2181.
Wan JP, Cao S., Liu Y. Base-promoted synthesis of N-substituted 1, 2, 3-triazoles via enaminone–azide cycloaddition involving Regitz diazo transfer //Organic letters. – 2016. – T. 18. – №. 23. – C. 6034-6037.
Quiñones RE et al. Direct synthesis of β - aminoenals through reaction of 1, 2, 3-triazine with secondary amines //Organic letters. – 2017. – T. 19. – №. 13. – C. 3568-3571.
Mart M., Trzeciak AM The synthesis of β -enaminones using trialkylamines and a Pd/DNA catalyst //Molecular Catalysis. – 2021. – T. 502. – C. 111365.
Xu SL, Li CP, Li JH Solid-state synthesis of β -enamino ketones from solid 1, 3-dicarbonyl compounds and ammonium salts or amines // Synlett . – 2009. – T. 2009. – №. 05. – C. 818-822.
Zeng X. et al. Metal-free method for direct synthesis of functionalized β - Ketoenamines //The Journal of Organic Chemistry. – 2019. – T. 84. – №. 6. – C. 3656-3661.
Wang L. et al. Direct access to α - oxoketene aminals via copper-catalyzed formal oxyaminalization of alkenes under mild conditions //Organic letters. – 2019. – T. 21. – №. 7. – C. 2223-2226.
Wu W. et al. Fe-Catalyzed enaminone synthesis from ketones and amines //Organic & Biomolecular Chemistry. – 2019. – T. 17. – №. 28. – C. 6753-6756.
Khudoiberdieva A. et al. - Synthesis of enaminones based on acetylacetone, homoveratrilamine and aromatic aldehydes // Universum. – 2024. – T. 2. – №. 6(120). – C. 40-45.