Home / Publications / Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles

Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles

Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
Elena V Ivanova 1
Elena V Ivanova
Nadezhda Victorovna Semenova 1
Nadezhda Victorovna Semenova
Inna Valeryevna Tatarinova 1
Inna Valeryevna Tatarinova
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
Published 2015-03-06
CommunicationVolume 25, Issue 2, 131-132
12
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Schmidt E. Y. et al. Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles // Mendeleev Communications. 2015. Vol. 25. No. 2. pp. 131-132.
GOST all authors (up to 50) Copy
Schmidt E. Y., Ivanova E. V., Semenova N. V., Tatarinova I. V., Ushakov I. A., Trofimov B. A. Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles // Mendeleev Communications. 2015. Vol. 25. No. 2. pp. 131-132.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2015.03.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.03.018
TI - Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles
T2 - Mendeleev Communications
AU - Schmidt, Elena Yur'evna
AU - Ivanova, Elena V
AU - Semenova, Nadezhda Victorovna
AU - Tatarinova, Inna Valeryevna
AU - Ushakov, Igor Alekseevich
AU - Trofimov, Boris Aleksandrovich
PY - 2015
DA - 2015/03/06
PB - Mendeleev Communications
SP - 131-132
IS - 2
VL - 25
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Schmidt,
author = {Elena Yur'evna Schmidt and Elena V Ivanova and Nadezhda Victorovna Semenova and Inna Valeryevna Tatarinova and Igor Alekseevich Ushakov and Boris Aleksandrovich Trofimov},
title = {Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.03.018},
number = {2},
pages = {131--132},
doi = {10.1016/j.mencom.2015.03.018}
}
MLA
Cite this
MLA Copy
Schmidt, Elena Yur'evna, et al. “Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles.” Mendeleev Communications, vol. 25, no. 2, Mar. 2015, pp. 131-132. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.03.018.

Abstract

The sequential reaction of ketones with phenylacetylene in the presence of KOH/DMSO system followed by the treatment of the reaction mixture with HCl and monosubstituted hydrazines leads to pyrazolines and pyrazoles in up to 87% total yield.

References

1.
Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction
Trofimov B., Schmidt E., Ushakov I., Zorina N., Skital'tseva E., Protsuk N., Mikhaleva A.
Chemistry - A European Journal, 2010
4.
Schmidt E.Y., Zorina N.V., Tarasova O.A., Ushakov I.A., Trofimov B.A.
Mendeleev Communications, 2013
5.
A One-Pot Approach to Δ2-Isoxazolines from Ketones and Arylacetylenes
Schmidt E.Y., Tatarinova I.V., Ivanova E.V., Zorina N.V., Ushakov I.A., Trofimov B.A.
Organic Letters, 2012
6.
Schmidt E.Y., Zorina N.V., Ivanova E.V., Tatarinova I.V., Ushakov I.A., Mikhaleva A.I., Trofimov B.A.
Mendeleev Communications, 2013
7.
Reactivity of o-styryloxazolines with nucleophiles
Seijas J.A., Vazquez-Tato M.P., Castedo L., Estevez R.J., Ruiz M.
Journal of Organic Chemistry, 1992
8.
Organolithium additions to styrene are synthetically viable
Wei X., Taylor R.J.
Chemical Communications, 1996
9.
Synthesis of β-phenylethylamines from styrene derivatives
Seijas J.A., Vázquez-Tato M.P., Entenza C., Montserrat Martínez M., Ònega M.G., Veiga S.
Tetrahedron Letters, 1998
11.
10.1016/j.mencom.2015.03.018_sbref0025b
Elkanzi
Int. J. Res. Pharm. Biomed. Sci., 2013
12.
A versatile building block for pyrazole–pyrrole hybrid macrocycles
Katsiaouni S., Dechert S., Brückner C., Meyer F.
Chemical Communications, 2007
13.
Diphosphines and pyrazole/pyrazolate-type ligands as building blocks in luminescent Au(I) complexes
Mayoral M.J., Ovejero P., Criado R., Cristina Lagunas M., Pintado-Alba A., Rosario Torres M., Cano M.
Journal of Organometallic Chemistry, 2011
14.
Polycatenar pyrazole and pyrazolate ligands as building blocks of new columnar Pd(ii) metallomesogens
Cuerva C., Campo J.A., Ovejero P., Torres M.R., Cano M.
Dalton Transactions, 2014