Regio- and stereoselective synthesis of isoindolin-1-ones via electrophilic cyclization.
[reaction: see text] A variety of substituted isoindolin-1-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICl, I(2), and NBS. In a few cases, substituted isoquinolin-1-ones were obtained as the major product instead. This methodology accommodates various alkynyl amides and functional groups and has been successfully extended to heterocyclic starting materials. This chemistry has been successfully applied to the synthesis of a biologically interesting alkaloid, cepharanone B.
Yao
Tuanli
T
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Larock
Richard C
RC
D034341:Aristolochic Acids / Q000138:chemical synthesis / Q000737:chemistry; D001549:Benzamides / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D034341:Aristolochic Acids; D001549:Benzamides; D007211:Indoles; C064674:aristololactam BII; C057812:indoline; C037689:benzamide