A simple method for the rapid synthesis of 2-amino-7,7-dimethyl-5-oxo-1,4-diaryl-hexahydroquinoline-3-carboxamide derivatives

• Published in: Journal of the Iranian Chemical Society 2020-09, Vol.17 (9), p.2267-2274
• Main Authors: Hosseini, Fahimeh Sadat, Bayat, Mohammad
• Format: Article
• Language: English
• Subjects: Aldehydes; Analytical Chemistry; Aniline; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; Derivatives; Ethanol; Inorganic Chemistry; Michael reaction; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Physical Chemistry; Piperidine
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-020-01920-3

Simple synthesis of oxoquinoline carboxamide derivatives via one-pot, multi-component reaction of enaminones derived from the addition of dimedone to various anilines with aromatic aldehydes and cyanoacetamide is described. Optimal reaction conditions for the synthesis of products were obtained, when EtOH/H 2 O (1:1) was used as the solvent at 80 °C, in the presence of piperidine as the catalyst. The reactions are completed within 5–25 min, in good to high yields (74–85%). This protocol involves Michael reaction, imine-enamine tautomerization, and cyclization sequences. The structures of products were deduced from their IR, mass, 1 H NMR, and 13 C NMR spectra. This method includes some important aspects including simple operation under mild conditions, easy accessibility of reactants, workup procedure, high atom economy, and the use of ethanol/water as a green media. Graphic abstract