Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
New green protocol for the efficient synthesis of pharmacologically relevant 4-amidyl-2-methyl-1,2,3,4-tetrahydroquinolines (THQs) through the domino type ABB’ imino Diels–Alder reaction in acidified water in the presence of sodium dodecyl sulphate (SDS) surfactant was developed for the first time....
- Autores:
- Tipo de recurso:
- Fecha de publicación:
- 2013
- Institución:
- Ministerio de Ciencia, Tecnología e Innovación
- Repositorio:
- Repositorio Minciencias
- Idioma:
- eng
- OAI Identifier:
- oai:repositorio.minciencias.gov.co:20.500.14143/34157
- Acceso en línea:
- http://repositorio.colciencias.gov.co/handle/11146/34157
- Palabra clave:
- Aceites vegetales
Biología vegetal
Aceites esenciales
Botánica
Bioquímica vegetal
Tecnología química
Química agrícola
Catalizadores
- Rights
- License
- http://purl.org/coar/access_right/c_f1cf
| Summary: | New green protocol for the efficient synthesis of pharmacologically relevant 4-amidyl-2-methyl-1,2,3,4-tetrahydroquinolines (THQs) through the domino type ABB’ imino Diels–Alder reaction in acidified water in the presence of sodium dodecyl sulphate (SDS) surfactant was developed for the first time. The influence of the SDS micelles and their different concentrations (5.0, 8.2 and 12.0 mM) on reactivity of the imino Diels–Alder reaction was studied. It was found that the best THQ yields (70–99%) are achieved above the critical micellar concentration (12 mM) using pH 1.0–2.5. This procedure resulted in a general and clean environmentally benign protocol to obtain the privileged diastereospecific cis 2,4-disubstituted THQ molecules of highest biological interest. |
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