Publication
Title
Synthesis of highly functionalized 1,6-dihydropyridines via the -catalyzed three-component cascade reaction of aldimines and two alkynes
Author
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.
Language
English
Source (journal)
Organic and biomolecular chemistry. - Cambridge, 2003, currens
Organic and biomolecular chemistry. - Cambridge, 2003, currens
Publication
Cambridge : 2018
ISSN
1477-0520 [print]
1477-0539 [online]
Volume/pages
16 :17 (2018) , p. 3241-3247
ISI
000431425800021
Pubmed ID
29664093
Full text (Publisher's DOI)
Full text (open access)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 25.04.2018
Last edited 21.09.2021
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