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Access to 2,3-diaryl-4-nitrothiochroman S,S-dioxides from 3-nitrobenzo[b]thiophene |
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| Authors: | Lara BianchiMassimo Maccagno Giovanni PetrilloEgon Rizzato Fernando SancassanDomenico Spinelli Cinzia Tavani |
| Institution: | a Dipartimento di Chimica e Chimica Industriale, Università di Genova, Via Dodecaneso 31, I-16146 Genova, Italy b Dipartimento di Chimica Organica ‘A. Mangini’, Università di Bologna, Via S. Giacomo 11, I-40126 Bologna, Italy c Dipartimento di Chimica ‘G. Ciamician’, Università di Bologna, Via Selmi 2, I-40126 Bologna, Italy |
| 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 1H NMR investigation, backed by molecular-mechanics calculations, has also been accomplished. |
| Keywords: | Thiochromans 3-Nitrobenzo[b]thiophene Ring-opening/ring-closing reactions Ring enlargement Conformations |
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