41419-45-8Relevant academic research and scientific papers
Mn(III)-mediated formal [3+3]-annulation of vinyl azides and cyclopropanols: A divergent synthesis of azaheterocycles
Wang, Yi-Feng,Toh, Kah Kah,Ng, Eileen Pei Jian,Chiba, Shunsuke
supporting information; experimental part, p. 6411 - 6421 (2011/06/19)
Mn(III)-mediated formal [3+3]-annulation has been developed using readily available vinyl azides and cyclopropanols with a wide range of substituents. Vinyl azides were successfully applied as a three-atom unit including one nitrogen to prepare pyridines and σ-lactams by the reactions with monocyclic cyclopropanols as well as to construct 2-azabicyclo[3.3.1] and 2-azabicyclo[4.3.1] frameworks with bicyclic cyclopropanols, bicyclo[3.1.0]hexan-1-ols, and bicyclo[4.1.0]heptan-1-ols. These reactions were initiated by a radical addition of β-carbonyl radicals, generated by the one-electron oxidation of cyclopropanols with Mn(III), to vinyl azides to give iminyl radicals, which cyclized with the intramolecular carbonyl groups. In addition, application of the present methodology to a synthesis of the quaternary indole alkaloid, melinonine-E, was accomplished.
