Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs) via proline-catalyzed direct Mannich-cyclization/domino oxidation–reduction sequence: application for medicinally important N-heterocycles
| Autor: | Nisar A. Mir, Deepika Singh, Indresh Kumar, Panduga Ramaraju |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
General Chemical Engineering Enantioselective synthesis Sequence (biology) Oxidation reduction General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Domino 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Organic chemistry Glutaraldehyde Proline |
| Zdroj: | RSC Advances. 6:60422-60432 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c6ra12965j |
| Popis: | An enantioselective multi-component synthesis of 1,2,5,6-tetrahydropyridines (THPs) has been developed through a one-pot domino-process. This transformation proceeds through proline-catalyzed direct Mannich reaction-cyclization of glutaraldehyde with in situ generated imines, followed by site-selective oxidation–reduction sequence under mild conditions. Chiral 1,2,5,6-THPs are obtained in good to high yields (up to 80%) and with the excellent enantioselectivity (up to 98 : 2 er). The usefulness of this operationally simple method is also shown to synthesize other medicinally important nitrogen-heterocycles. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|