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Structural elucidation and complete assignment of a novel class of sulfonamides: bridgehead tricyclic sultams
Author(s) -
Jolivet Catherine,
Long Daniel D.,
Dahl Russel S.,
Termin Andreas P.
Publication year - 2002
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1006
Subject(s) - chemistry , heteronuclear molecule , two dimensional nuclear magnetic resonance spectroscopy , intramolecular force , nuclear overhauser effect , nuclear magnetic resonance spectroscopy , stereochemistry , olefin fiber , derivatization , molecule , heteronuclear single quantum coherence spectroscopy , computational chemistry , organic chemistry , polymer , high performance liquid chromatography
Endocyclic sulfonamide templates bearing both an exocyclic ketone function and an internal olefin underwent reaction with a variety of hydroxylamines to effect an intramolecular nitrone–olefin cycloaddition to afford a new class of compounds suitable for derivatization by high‐throughput medicinal chemistry. Structural elucidation via complete assignment of the 1 H and 13 C NMR spectra of this new class of compounds was achieved using gradient‐COSY, gradient heteronuclear multiple quantum‐coherence spectroscopy and gradient heteronuclear multiple bond correlation spectroscopy. Additionally, double pulsed field gradient spin echo–nuclear Overhauser effect experiments were carried out in order to study the spatial conformation of this new type of molecule and assess the stereo‐ and regio‐selectivity of the chemical transformation. The unequivocal molecular framework and structural conformation was confirmed by X‐ray diffraction. Copyright © 2002 John Wiley & Sons, Ltd.