David E Stephens1, Oleg V Larionov1. 1. Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
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.
A base-mediated regioselective electrophilic addition of n class="Chemical">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 saltsasnitrogenous electrophiles.
Authors: Klement Foo; Timothy Newhouse; Ikue Mori; Hiromitsu Takayama; Phil S Baran Journal: Angew Chem Int Ed Engl Date: 2011-02-17 Impact factor: 15.336