title: Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.
abstract: A base-mediated regioselective electrophilic addition of arenediazonium salts at the C3-position of tryptamines followed by cyclization provides an efficient entry to C3-nitrogenated hexahydropyrrolo[2,3-b]indoles (HPIs) that can subsequently be transformed into 3-arylhexahydropyrrolo[2,3-b]indoles and other HPI derivatives. The reaction is the first example of a 1,2-diamination that utilizes easily accessible arenediazonium salts as nitrogenous electrophiles.
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: David E
authors.initials: DE
authors.lastname: Stephens
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Larionov
keywords: Diazonium compounds; Electrophilic addition; Hydrazines; Pyrroloindolines; Synthetic methods