ChemInform Abstract: Aqueous SDS Micelle-Promoted Acid-Catalyzed Domino ABB′ Imino Diels-Alder Reaction: A Mild and Efficient Synthesis of Privileged 2-Methyl-tetrahydroquinoline Scaffolds

Autor:	Carlos A. Martínez Bonilla, Diego R. Merchan Arenas, Vladimir V. Kouznetsov
Rok vydání:	2013
Předmět:	Green chemistry Aqueous solution Pulmonary surfactant Chemistry Critical micelle concentration Sodium chemistry.chemical_element Reactivity (chemistry) General Medicine Medicinal chemistry Micelle Diels–Alder reaction
Zdroj:	ChemInform. 44
ISSN:	0931-7597
DOI:	10.1002/chin.201339160
Popis:	A 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3887efad56312119524de2df06da9281 https://doi.org/10.1002/chin.201339160 Zobrazit plný text záznamu Plný text