Access to 2,3-diaryl-4-nitrothiochroman S,S-dioxides from 3-nitrobenzo[b]thiophene

• DOI: 10.1016/j.tet.2011.08.038
• Publication Date: 2011-08-22T20:44:35Z
• Authors: Lara Bianchi; Massimo Maccagno; Giovanni Petrillo; Egon Rizzato; Fernando Sancassan; Domenico Spinelli; Cinzia Tavani
• Keywords: Base (topology); Molecular mechanics

Abstract The base-induced cyclization of ( E )-2-aryl-1-[2-(benzylsulfonyl)phenyl]-1-nitroethenes to polysubstituted thiochroman S , S -dioxides exhibits a diastereoselectivity that can be oriented towards a selected isomer by means of appropriate adjustments of the experimental conditions. The interest of such a result also rests on the promising pharmacological activity of the products, whose structure encompasses different well-acknowledged pharmacophores. A conformational 1 H NMR investigation, backed by molecular-mechanics calculations, has also been accomplished.