Convenient,DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP |
| |
| Affiliation: | 1. M. V. Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, 119454 Moscow, Russian Federation;2. Peptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran;3. Medical Biology Research Center, Kermanshah University of Medical Sciences, P. O. Box 67155-1616, Kermanshah, Iran;4. St. Petersburg State University, 199034 St. Petersburg, Russian Federation;5. Immanuel Kant Baltic Federal University, 236016 Kaliningrad, Russian Federation;1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation;2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation;1. Mental Health Research Institute, Tomsk National Research Medical Center, Russian Academy of Sciences, 634050 Tomsk, Russian Federation;2. Siberian State Medical University, 634050 Tomsk, Russian Federation;3. National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation;4. Scientific Center for Mental Health, 115522 Moscow, Russian Federation;5. E. D. Goldberg Research Institute of Pharmacology and Regenerative Medicine, Tomsk National Research Medical Center, Russian Academy of Sciences, 634028 Tomsk, Russian Federation;1. Institute of Structural Macrokinetics and Materials Science, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;2. N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 119991 Moscow, Russian Federation;1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. National Research Center ‘Kurchatov Institute’, 123182 Moscow, Russian Federation;3. Institute of Chemical Reagents and High Purity Chemical Substances, National Research Center ‘Kurchatov Institute’, 107076 Moscow, Russian Federation;4. N. N. Blokhin National Medical Research Center of Oncology of the Ministry of Health of the Russian Federation, 115478 Moscow, 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 |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
