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


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2016-06

AUTHORS

I. E. Mikhailov, A. A. Kolodina, G. A. Dushenko, V. V. Tkachev, S. M. Aldoshin, V. I. Minkin

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. More... »

PAGES

191-194

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s0012500816060082

DOI

http://dx.doi.org/10.1134/s0012500816060082

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1002915672


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