A Synthetic Route to Tetrahydro-1H-azepino[4,3,2-cd]indoles via Ring-Opening Cyclization of Activated Azetidines with 4-Bromoindole: Toward a Vasopressin V2 Receptor Antagonist
Gaurav Goswami,
Bharat Singh,
Imtiyaz Ahmad Wani
et al.
Abstract:A simple one-pot, two-step strategy for the synthesis of tetrahydro-1H-azepino[4,3,2-cd]indoles via Lewis acidcatalyzed S N 2-type ring opening of activated azetidines with 4-bromoindole, followed by a Pd-catalyzed intramolecular C−N cyclization reaction, with good to excellent yields is described. Utilizing this protocol, the vasopressin V2 receptor antagonist precursor has been synthesized easily. Enantioenriched tetrahydro-1H-azepino[4,3,2-cd]indoles were obtained by starting from enantiopure azetidine.
Set email alert for when this publication receives citations?
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.