Home / Publications / Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles

Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles

Margarita Alekseevna Epishina 1
Margarita Alekseevna Epishina
Alexander Sergeyevich Kulikov 1
Alexander Sergeyevich Kulikov
Nikolai V Ignat'ev 2
Nikolai V Ignat'ev
Michael Schulte 2
Michael Schulte
Nina Nikolaevna Makhova 1
Nina Nikolaevna Makhova
2 Ionic Liquid Research Laboratory, Merck KGaA, Darmstadt, Germany
Published 2011-11-10
CommunicationVolume 21, Issue 6, 334-336
18
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Epishina M. A. et al. Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles // Mendeleev Communications. 2011. Vol. 21. No. 6. pp. 334-336.
GOST all authors (up to 50) Copy
Epishina M. A., Kulikov A. S., Ignat'ev N. V., Schulte M., Makhova N. N. Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles // Mendeleev Communications. 2011. Vol. 21. No. 6. pp. 334-336.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2011.11.014
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.11.014
TI - Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles
T2 - Mendeleev Communications
AU - Epishina, Margarita Alekseevna
AU - Kulikov, Alexander Sergeyevich
AU - Ignat'ev, Nikolai V
AU - Schulte, Michael
AU - Makhova, Nina Nikolaevna
PY - 2011
DA - 2011/11/10
PB - Mendeleev Communications
SP - 334-336
IS - 6
VL - 21
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2011_Epishina,
author = {Margarita Alekseevna Epishina and Alexander Sergeyevich Kulikov and Nikolai V Ignat'ev and Michael Schulte and Nina Nikolaevna Makhova},
title = {Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.11.014},
number = {6},
pages = {334--336},
doi = {10.1016/j.mencom.2011.11.014}
}
MLA
Cite this
MLA Copy
Epishina, Margarita Alekseevna, et al. “Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles.” Mendeleev Communications, vol. 21, no. 6, Nov. 2011, pp. 334-336. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.11.014.

Abstract

Interaction of aliphatic, aromatic and heteroaromatic nitriles with NaN3 or activated nitriles with organic azides in ionic liquids affords the corresponding 5-mono- and 1,5-disubstituted tetrazoles, ionic liquids functioning both as a reaction medium and as a catalyst.

References

1.
R. N. Butler, in Comprehensive Heterocyclic Chemistry, 2nd edn., eds. A. R. Katritzky, C.W. Rees and E. F. Scriven, Pergamon Press, Oxford, 1996, vol. 4, p. 621.
2.
U. Heinemann, W. Brandes and G. Haenssler, Ger. Patent 3640153, 1988 (Chem. Abstr., 1988, 109, 93026).
3.
V. A. Ostrovskii and G. I. Koldobskii, Ross. Khim. Zh. (Zh. Ross. Khim. Ob-va im. D. I. Mendeleeva), 1997, 41, 84.(in Russian).
4.
An Improved Synthesis of 5-Substituted Tetrazoles
Finnegan W.G., Henry R.A., Lofquist R.
Journal of the American Chemical Society, 1958
5.
V. V. Filichev, A.A. Malin, M.V. Yas’ko, M.B. Shcherbinin and V. A. Ostrovskii, Zh. Org. Khim., 1998, 34, 477.(in Russian).
6.
Rearrangement Reactions of (Hydroxyphenyl)carbenes
Kumar A., Narayanan R., Shechter H.
Journal of Organic Chemistry, 1996
8.
Efficient synthesis of 5-(4'-methyl[1,1'-biphenyl]-2-yl)-1H-tetrazole
Russell R.K., Murray W.V.
Journal of Organic Chemistry, 1993
9.
Preparation of 5-Substituted 1H-Tetrazoles from Nitriles in Water
Demko Z.P., Sharpless K.B.
Journal of Organic Chemistry, 2001
11.
Tetrazole analogues of physiologically or pharmacologically active carboxylic acids
Brouwer-Van Straaten B., Solinger D., van de Westeringh C., Veldstra H.
Recueil des Travaux Chimiques des Pays-Bas, 2010
14.
Tetrazole Analogs of Pyridinecarboxylic Acids1
McMANUS J.M., HERBST R.M.
Journal of Organic Chemistry, 1959
15.
Synthesis of New Tetrazole-Substituted Pyroaminoadipic and Pipecolic Acid Derivatives
Lenda F., Guenoun F., Tazi B., Ben larbi N., Allouchi H., Martinez J., Lamaty F.
European Journal of Organic Chemistry, 2005
18.
Microwave-assisted synthesis and transformations of sterically hindered 3-(5-tetrazolyl)pyridines
Lukyanov S.M., Bliznets I.V., Shorshnev S.V., Aleksandrov G.G., Stepanov A.E., Vasil'ev A.A.
Tetrahedron, 2006
19.
5-Trifluoromethyltetrazole and Its Derivatives
Norris W.P.
Journal of Organic Chemistry, 1962
21.
Safe and fast tetrazole formation in ionic liquids
Schmidt B., Meid D., Kieser D.
Tetrahedron, 2007
24.
Practical Synthesis of 5-Substituted Tetrazoles under Microwave Irradiation
Roh J., Artamonova T., Vávrová K., Koldobskii G., Hrabálek A.
Synthesis, 2009
26.
Synthesis of 5-ketotetrazoles under high pressure
Zavarzin I.V., Zhulin V.M., Yarovenko V.N., Krayushkin M.M.
Russian Chemical Bulletin, 1988
27.
5-Tetrazolecarboxamides and their salts: new orally active antiallergy agents
Klaubert D.H., Sellstedt J.H., Guinosso C.J., Bell S.C., Capetola R.J.
Journal of Medicinal Chemistry, 1981