Synthesis of highly functionalized 1,6-dihydropyridines via the Zn(OTf) 2 -catalyzed three-component cascade reaction of aldimines and two alkynes (IA 2 -coupling)
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 ali...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2018, Vol.16 (17), p.3241-3247 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Shehzadi, Syeda Aaliya Vande Velde, Christophe M L Saeed, Aamer Abbaspour Tehrani, Kourosch |
| description | 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. |
| doi_str_mv | 10.1039/c8ob00195b |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2018, Vol.16 (17), p.3241-3247 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2026418610 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aliphatic compounds Alkynes Cascade chemical reactions Chemical synthesis Dihydropyridine Electrons Zinc |
| title | Synthesis of highly functionalized 1,6-dihydropyridines via the Zn(OTf) 2 -catalyzed three-component cascade reaction of aldimines and two alkynes (IA 2 -coupling) |
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