Synthesis of highly functionalized 1, 6-dihydropyridines via the Zn(OTf)2-catalyzed three-component cascade reaction of aldimines and two alkynes (IA2-coupling). Issue 17 (17th April 2018)

• Record Type: Journal Article
• Authors: Shehzadi, Syeda Aaliya; Vande Velde, Christophe M. L.; Saeed, Aamer; Abbaspour Tehrani, Kourosch
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 17(2018)
• Page Start: 3241
• Page End: 3247
• Publication Date: 2018-04-17
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00195b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : One pot Zn(ii )-catalyzed imine–alkyne–alkyne coupling. Abstract : A zinc(ii ) triflate catalyzed three component synthesis of 1, 6-dihydropyridines, involving aldimines, alkynes and electron-deficient dimethyl acetylenedicarboxylate (DMAD), in good to excellent yields has been described. Besides a range of different N -substituents, a variety of both aromatic and aliphatic alkynes could be used. The application of electron-deficient propiolates instead of DMAD resulted in regiospecific incorporation of the ester functionality on the 1, 6-dihydropyridine ring. The reaction proceeds via a cascade reaction involving nucleophilic addition of the metal acetylide to the imine, followed by the addition of the intermediately formed propargylic amine to the electron-deficient alkyne and subsequent 6- endo dig cyclization.