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

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

Alexei Yur'evich Lukin 1
Alexei Yur'evich Lukin
, 
Anna Gennad'evna Nichugovskaya 1
Anna Gennad'evna Nichugovskaya
, 
Lyubov V Vinogradova 1
Lyubov V Vinogradova
, 
Kristina Yuryevna Komarova 1
Kristina Yuryevna Komarova
, 
Saeed Balalaie 2, 3
Saeed Balalaie
, 
Dmitry Viktorovich Dar’in 4
Dmitry Viktorovich Dar’in
, 
Mikhail Yur'evich Krasavin 4, 5
Mikhail Yur'evich Krasavin
1 M.V. Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, Moscow, Russian Federation
2 Department of Chemistry, K.N. Toosi University of Technology, Tehran, Iran
3 Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran
4 Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
5 Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation
10.1016/j.mencom.2023.06.004
Published 2023-06-13
Communication , Volume 33, Issue 4, 455-457
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Lukin A. Y. et al. Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 455-457.
GOST all authors (up to 50) Copy
Lukin A. Y., Nichugovskaya A. G., Vinogradova L. V., Komarova K. Y., Balalaie S., Dar’in D. V., Krasavin M. Y. Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 455-457.
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TY - JOUR
DO - 10.1016/j.mencom.2023.06.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.004
TI - Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP
T2 - Mendeleev Communications
AU - Lukin, Alexei Yur'evich
AU - Nichugovskaya, Anna Gennad'evna
AU - Vinogradova, Lyubov V
AU - Komarova, Kristina Yuryevna
AU - Balalaie, Saeed
AU - Dar’in, Dmitry Viktorovich
AU - Krasavin, Mikhail Yur'evich
PY - 2023
DA - 2023/06/13
PB - Mendeleev Communications
SP - 455-457
IS - 4
VL - 33
ER -
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@article{2023_Lukin,
author = {Alexei Yur'evich Lukin and Anna Gennad'evna Nichugovskaya and Lyubov V Vinogradova and Kristina Yuryevna Komarova and Saeed Balalaie and Dmitry Viktorovich Dar’in and Mikhail Yur'evich Krasavin},
title = {Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.004},
number = {4},
pages = {455--457},
doi = {10.1016/j.mencom.2023.06.004}
}
MLA
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Lukin, Alexei Yur'evich, et al. “Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP.” Mendeleev Communications, vol. 33, no. 4, Jun. 2023, pp. 455-457. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.004.

Keywords

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

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.

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