Lewis Acid Promoted Oxonium Ion Driven Carboamination of Alkynes for the Synthesis of 4-Alkoxy Quinolines
| Autor: | Yogesh G. Shelke, Priyanka A. Adate, Santosh K. Nanda, Santosh J. Gharpure |
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| Rok vydání: | 2017 |
| Předmět: |
Stereochemistry
Alkyne 010402 general chemistry 01 natural sciences High yielding chemistry.chemical_compound Divergent Synthesis Stereoselective-Synthesis Molecule Lewis acids and bases Substituted Quinolines One-Pot Synthesis Catalyzed Cyclization chemistry.chemical_classification 010405 organic chemistry Organic Chemistry Acridone Alkaloids Functionalized Quinolines Combinatorial chemistry 0104 chemical sciences chemistry Cyclic ether Functional group Facile Synthesis Alkoxy group Polysubstituted Quinolines Regioselective Synthesis Oxonium ion |
| Zdroj: | The Journal of Organic Chemistry. 82:2067-2080 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.6b02896 |
| Popis: | Lewis acid mediated multisegment coupling cascade is designed for the synthesis of densely substituted 4-alkoxy quinolines via an oxonium ion triggered alkyne carboamination sequence involving C-C and C-N bond formations. Cyclic ether fused-quinolines could also be accessed using this fast, operationally simple, high yielding, chemoselective and functional group tolerant method. Versatility and utility of this methodology is demonstrated by postfunctionalization of products obtained and its use in synthesis of potent drug molecules. |
| Databáze: | OpenAIRE |
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