Synthesis and structure of 5,7-Di(tert-butyl)-2-(8-methanesulfonyloxyquinolin-2-yl)-1,3-tropolone

Abstract

5,7-Di(tert-butyl)-2-(8-methanesulfonyloxyquinolin-2-yl)-1,3-tropolone whose structure was established by X-ray diffraction analysis and confirmed by ¹H and ¹³C NMR, IR spectroscopy, and mass spectrometry, was obtained by the reaction of 2-methyl-8-methanesulfonyloxyquinoline with 3,5-di(tert-butyl)-1,2-benzoquinone. According to X-ray diffraction study, this sulfonyloxyquinolinotropolone exists in the NH tautomeric form with methanesulfonyloxy group in the exo position to the tropolone ring and the sixmembered chelate ring produced by the quinoline and tropolone moieties stabilized by strong intramolecular hydrogen bond. The strong intramolecular hydrogen bond between the phenolic oxygen atom and the six-membered chelate ring provides supplementary contribution to the stabilization of the NH tautomeric form.