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Title
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Synthesis of highly functionalized 1,6-dihydropyridines via the -catalyzed three-component cascade reaction of aldimines and two alkynes
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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Organic and biomolecular chemistry. - Cambridge, 2003, currens
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Publication
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Cambridge
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Royal Society of Chemistry
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2018
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ISSN
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1477-0520
[print]
1477-0539
[online]
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DOI
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10.1039/C8OB00195B
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Volume/pages
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16
:17
(2018)
, p. 3241-3247
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ISI
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000431425800021
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Pubmed ID
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29664093
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Full text (Publisher's DOI)
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Full text (open access)
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