A. Lukin, A. Nichugovskaya, L. Vinogradova, K. Komarova, S. Balalaie, D. Dar’in, M. Krasavin, “Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1<i>H</i>-imidazoles in wet NMP”, Mendeleev Commun., 2023, Volume 33, Issue 4,Pages <nobr>455

Communications

Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP

A. Lukin^a, A. Nichugovskaya^a, L. Vinogradova^a, K. Komarova^a, S. Balalaie^bc, D. Dar’in^d, M. Krasavin^de

^a M.V. Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, Moscow, Russian Federation
^b Department of Chemistry, K.N. Toosi University of Technology, Tehran, Iran
^c Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran
^d Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
^e Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation

Abstract: During attempts to involve 5-methyl-2-phenyl-1-(3-phenyl-prop-2-yn-1-yl)-1H-imidazole in a base-promoted, allene-mediated cyclization of the alkyne moiety onto the nearby aromatic ring, substantial amount of the ketone resulting from hydration of the alkyne with adventitious water was discovered. The formation of the ketone of the anti-Markovnikov alkyne hydration was developed into a preparative method. This method, alternative to the common acid-and metal-catalyzed approaches, may be of particular utility when alkyne hydration needs to be performed in the presence of acid-labile groups.

Keywords: imidazoles, propargylic amines, alkynes, hydration, anti-Markovnikov, 1,8-diazabicyclo[5.4.0]undec-7-ene.

Language: English

DOI: 10.1016/j.mencom.2023.06.004

	*Supplementary materials:*
		Supplementary_data_1.pdf	4.7 Mb