A novel asymmetric synthesis of atropisomeric 6-aryl pyrazinones via an unusual chirality transfer process. New chiral ligands for the GABAA/Chloride ionophore complex

Autor:	William Watt, Ronald B. Gammill, Stephen A. Mizsak, Lester A. Dolak, Thomas M. Judge, John Tulinsky
Rok vydání:	1995
Předmět:	Atropisomer Stereochemistry Aryl Organic Chemistry Ionophore Enantioselective synthesis Biochemistry Toluene chemistry.chemical_compound chemistry Chlorobenzene Drug Discovery Acetonitrile Chirality (chemistry)
Zdroj:	Tetrahedron Letters. 36:2017-2020
ISSN:	0040-4039
Popis:	Cyclization of ( S , S )- α -[(1-phenylethyl)amino]- α -(2-iodophenyl)acetonitrile 3a with (COCl) 2 in toluene or chlorobenzene afforeded the atropisomeric pyrazinone ( aS , S ) 6-(2-α-iodophenyl)-3,5-dichloro-1-(1-phenylethyl)-2(1H)-pyrazinone 7a in 57% yield. With smaller ortho substituents, mixtures of atropisomers were obtained. Stereochemical assignments were made via X-Ray and NOE experiments.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::eff2345756001ff6a17273d17d49da76 https://doi.org/10.1016/0040-4039(95)00216-y Zobrazit plný text záznamu Full Text from ScienceDirect