Access to 2,3-diaryl-4-nitrothiochroman S,S-dioxides from 3-nitrobenzo[b]thiophene
| Autor: | Domenico Spinelli, Giovanni Petrillo, Fernando Sancassan, Lara Bianchi, Egon Rizzato, Cinzia Tavani, Massimo Maccagno |
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| Rok vydání: | 2011 |
| Předmět: |
Ring-opening/ring-closing reactions
Chemistry Stereochemistry Ring enlargement Organic Chemistry Biological activity 3-Nitrobenzo[b]thiophene Thiochromans 3-Nitrobenzo[b]thiophene Ring-opening/ring-closing reactions Ring enlargement Conformations Biochemistry Conformations chemistry.chemical_compound Drug Discovery Proton NMR Thiophene Thiochromans Pharmacophore |
| Zdroj: | Tetrahedron. 67:8160-8169 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2011.08.038 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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