Aryl Radical Cyclizations of 1-(2‘-Bromobenzyl)isoquinolines with AIBN−Bu3SnH: Formation of Aporphines and Indolo[2,1-a]isoquinolines

Autor:	Takashi Tatsuzawa, Masao Tokuda, Shiho Uchiito, Rika Harada, Kazuhiko Orito, Yoshitaka Satoh
Rok vydání:	2000
Předmět:	chemistry.chemical_compound Aryl radical chemistry Organic Chemistry Alkoxy group Aporphines Physical and Theoretical Chemistry Biochemistry Medicinal chemistry Radical cyclization Steric repulsion
Zdroj:	Organic Letters. 2:307-310
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol990360v
Popis:	Radical cyclization of alkoxy-substituted 1-(2‘-bromobenzyl)-3,4-dihydroisoquinolines 1 with AIBN−Bu3SnH gave 6a,7-dehydroaporphines 2 preferentially. A steric repulsion between the respective alkoxy groups at the 7- and 3‘-positions gave 5,6-dihydroindolo[2,1-a]isoquinolines 3 in a “disfavored” 5-endo cyclization mode. Radical cyclizations of the related substrates, such as 1-(2‘-bromobenzoyl)isoquinolines or 1-(2‘-bromo-α-hydroxybenzyl)isoquinolines, were also found to give the corresponding oxoaporphines or oxyaporphines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bb5c8e294d6b9e816bf059d6e26e9521 https://doi.org/10.1021/ol990360v Zobrazit plný text záznamu