S. K. Polyakova, T. V. Balashova, R. V. Rumyantcev, M. V. Arsenyev, G. K. Fukin, S. A. Chesnokov, “Utilizing <i>o</i>-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols”, Mendeleev Commun., 2021, Volume 31, Issue 2,Pages <nobr>262

This article is cited in 8 papers

Communications

Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols

S. K. Polyakova^ab, T. V. Balashova^a, R. V. Rumyantcev^a, M. V. Arsenyev^ab, G. K. Fukin^a, S. A. Chesnokov^a

^a G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhnii Novgorod, Russian Federation
^b N.I. Lobachevsky State University of Nizhni Novgorod, Nizhni Novgorod, Russian Federation

Abstract: Three new sterically hindered acridin-4-ols have been prepared by alkylation of anilines with 3,5-di-tert-butyl-6-methoxymethylcatechol followed by oxidation of the reaction mixture. Formation of the acridine moiety was found to occur in the course of oxidation of the intermediate (anilinomethyl)catechol on contact with air in the Et₂O/H₂O–KOH system. The molecular structure of two acridin-4-ols was determined by single-crystal X-ray diffraction.

Keywords: acridines, heterocyclization, quinone methides, alkylation, catechols, anilines, X-ray diffraction analysis.

Language: English

DOI: 10.1016/j.mencom.2021.03.040

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