SULFUR-CONTROLLED 5-EXO SELECTIVE ARYL RADICAL CYCLIZATION OF N-VINYLIC 2-BROMOBENZAMIDES - SYNTHESIS OF LENNOXAMINE AND CHILENINE

Authors
ISHIBASHI H KAWANAMI H IKEDA M
Citation
H. Ishibashi et al., SULFUR-CONTROLLED 5-EXO SELECTIVE ARYL RADICAL CYCLIZATION OF N-VINYLIC 2-BROMOBENZAMIDES - SYNTHESIS OF LENNOXAMINE AND CHILENINE, Journal of the Chemical Society. Perkin transactions. I, (6), 1997, pp. 817-821
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
6
Year of publication
1997
Pages
817 - 821
Database
ISI
SICI code
0300-922X(1997):6<817:S5SARC>2.0.ZU;2-1
Abstract
Bu(3)SnH-mediated aryl radical cyclisation of [2,2-bis(phenylsulfanyl) ethenyl]-2-bromobenzamides 12a-d and 16 takes place in a 5-exo manner to give exclusively the isoindolones 15a-d and 17, respectively. The i soindolone 17 is converted into lennoxamine and a key intermediate 20 for the synthesis of chilenine.