The 15N induced isotope shift as an effective tool for the structure elucidation of 2, 4 and 2, 5 di-substituted thiazoles. Issue 30 (22nd July 2015)

• Record Type: Journal Article
• Authors: Guzzo, Tatiana; Aramini, Andrea; Lillini, Samuele; Nepravishta, Ridvan; Paci, Maurizio; Topai, Alessandra
• Is Part Of: Tetrahedron letters. Volume 56:Issue 30(2015)
• Page Start: 4455
• Page End: 4458
• Publication Date: 2015-07-22
• Subjects: NMR spectroscopy -- 15N isotope shift -- 15N labeling -- Di-substituted thiazoles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.084
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 15 N isotope effects have been used for structural elucidation of the di-substituted thiazole 1 -DFL 23805, a novel and potent dual CXCR1/CXCR2 inhibitor, developed by Dompé within the MedChem program. The compound and its 15 N isotopologue have been synthesized according to the same proprietary procedure. The 1 H and 13 C NMR spectra have been measured. The isotope effects on chemical shifts and on coupling constants have been studied in detail. The collected data highlight a new perspective on the elucidation of disubstituted thiazole system, as only very few reference data have been published so far. All the results are consistent with the 2, 4 regioisomery assignment.