Microwave-assisted catalyst-free multicomponent one-pot green synthesis of highly functionalized aminocyanopyridines and (4-hydroxy)quinolines in aqueous medium and its in silico studies

Abstract

Microwave-assisted Catalyst-free three components one-pot green synthesis of highly functionalized aminocyanopyridine and (4-hydroxy)quinoline derivatives is reported using quinoline-3-carbaldehyde or chromene, malononitrile, and ammonium salt in the aqueous medium. The scalable...

One-Pot Synthesis of 4-Chloroquinolines via Bis(trichloromethyl) Carbonate and Triphenylphosphine Oxide-Mediated Cascade Reactions of N-Aryl Enaminones

“…Gray solid, mp 63−64 °C. 1 H NMR (300 MHz, CDCl 3 ) δ 7.88 (d, J = 9.0 Hz, 1H), 7.38 (dd, J 1 = 9.0 Hz, J 2 = 2.7 Hz, 1H), 7.07 (d, J = 2.7 Hz, 1H), 4.50 (q, J = 7.2 Hz, 2H), 3.11 (s, 6H), 2.65 (s, 3H),1.45 (t, J = 7.2 Hz, 3H); 13 8.38 (dd, J 1 = 8.7 Hz, J 2 = 1.8 Hz, 1H), 8.09 (d, J = 8.7 Hz, 1H), 4.54 (q, J = 7.2 Hz, 2H), 4.48 (q, J = 7.2 Hz, 2H), 2.76 (s, 3H), 1.47 (t, J = 7.2 Hz, 6H); 13 Ethyl 4-Chloro-2-methyl-6-(trifluoromethyl)quinoline-3-carboxylate (2i). Yield: 37% (117.4 mg).…”

“…The conventional synthesis of 4-chloroquinolines predominantly relies on the dehydroxychlorination of 4-hydroxyquinolines − (Scheme a) and the Vilsmeier reaction of 2-acetylanilines (Scheme b). These traditional approaches are fraught with challenges, including the limited availability of precursors, the necessity for excessive amounts of moisture-sensitive and hazardous acid chlorides, such as POCl 3 , and rigorous reaction conditions.…”