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

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...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2011-10, Vol.67 (42), p.8160-8169
Main Authors: Bianchi, Lara, Maccagno, Massimo, Petrillo, Giovanni, Rizzato, Egon, Sancassan, Fernando, Spinelli, Domenico, Tavani, Cinzia
Format: Article
Language:English
Subjects:
3-Nitrobenzo[ b]thiophene
Adjustment
Chemistry
Conformations
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Isomers
Mathematical analysis
Nuclear magnetic resonance
Organic chemistry
Preparations and properties
Rest
Ring enlargement
Ring-opening/ring-closing reactions
Tetrahedrons
Thiochromans
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.08.038