One-pot synthesis of highly diversified tetrahydropyridines by tandem condensation of aldehydes, amines, and β-ketoesters

• Published in: Tetrahedron 2012-01, Vol.68 (1), p.363-369
• Main Authors: Ramachandran, Rajamanickam, Jayanthi, Sampathkumar, Jeong, Yeon Tae
• Format: Article
• Language: English
• Subjects: Aldehydes; Amines; Catalysis; Catalysts: preparations and properties; Chemistry; Diffraction; Exact sciences and technology; General and physical chemistry; Graphs; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Hydrogen bonding; One-pot synthesis; Organic chemistry; Preparations and properties; Silica-supported boron trifluoride; Synthesis (chemistry); Tandem reaction; Tetrahedrons; Tetrahydropyridines; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; X-rays
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.09.105

Silica-supported boron trifluoride (BF3·SiO2) was used as an efficient and reusable catalyst for the synthesis of highly diversified tetrahydropyridines by one-pot multicomponent reactions of amines and aldehydes with β-ketoester. This method proceeds through the intermolecular Mannich reaction followed by intramolecular Mannich reaction. The observed hydrogen bonding interaction was studied in detail with single crystal X-ray diffraction analysis and Etter’s graph. Finally, this method has the advantage of easy work-up, convenient, relatively short reaction times and the products were isolated with high yields. [Display omitted]