Home / Publications / Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds

Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds

Dmitry Vladimirovich Davydov 1
Dmitry Vladimirovich Davydov
, 
Vladimir Vasilyvich Chernyshev 1
Vladimir Vasilyvich Chernyshev
, 
Viktor Borisovich Rybakov 1
Viktor Borisovich Rybakov
, 
Yurii Fedorovich Oprunenko 1
Yurii Fedorovich Oprunenko
, 
10.1016/j.mencom.2018.05.019
Published 2018-04-27
Communication , Volume 28, Issue 3, 287-289
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Davydov D. V. et al. Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 287-289.
GOST all authors (up to 50) Copy
Davydov D. V., Chernyshev V. V., Rybakov V. B., Oprunenko Y. F., Beletskaya I. P. Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 287-289.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.05.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.019
TI - Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds
T2 - Mendeleev Communications
AU - Davydov, Dmitry Vladimirovich
AU - Chernyshev, Vladimir Vasilyvich
AU - Rybakov, Viktor Borisovich
AU - Oprunenko, Yurii Fedorovich
AU - Beletskaya, Irina Petrovna
PY - 2018
DA - 2018/04/27
PB - Mendeleev Communications
SP - 287-289
IS - 3
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Davydov,
author = {Dmitry Vladimirovich Davydov and Vladimir Vasilyvich Chernyshev and Viktor Borisovich Rybakov and Yurii Fedorovich Oprunenko and Irina Petrovna Beletskaya},
title = {Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.019},
number = {3},
pages = {287--289},
doi = {10.1016/j.mencom.2018.05.019}
}
MLA
Cite this
MLA Copy
Davydov, Dmitry Vladimirovich, et al. “Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds.” Mendeleev Communications, vol. 28, no. 3, Apr. 2018, pp. 287-289. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.019.

Abstract

Modification of benzotriazoles with iodonium salts [diphenyl- and (E)-styrylphenyliodonium tosylates] occurs at the N1-position in the presence of K2CO3 as a base and CuI as a catalyst in CH2Cl2, whereas in the presence of stoichiometric amount of [Cu2(TMEDA)2(OH)2]Cl2 complex regioselective N2-modification proceeds. Two new CuI complexes based on benzotriazoles were synthesized and their crystal structures were determined by X-ray powder diffraction analysis.

References

1.
Properties and Synthetic Utility of N-Substituted Benzotriazoles
Katritzky A.R., Lan X., Yang J.Z., Denisko O.V.
Chemical Reviews, 1998
4.
The Benzotriazole Story
Dennis Hall C., Panda S.S.
Advances in Heterocyclic Chemistry, 2016
5.
Benzotriazole: An overview on its versatile biological behavior
Briguglio I., Piras S., Corona P., Gavini E., Nieddu M., Boatto G., Carta A.
European Journal of Medicinal Chemistry, 2015
6.
10.1016/j.mencom.2018.05.019_sbref0010b
Mishra
Int. J. Pharm. Technol. Biotechnol., 2015
8.
Palladium-Catalyzed Synthesis of 2-Aryl-2H-Benzotriazoles from Azoarenes and TMSN3
Khatun N., Modi A., Ali W., Patel B.K.
Journal of Organic Chemistry, 2015
9.
o-Nitrodiphenylamin und einige Derivate
Schöpff M.
Berichte der deutschen chemischen Gesellschaft, 1890
12.
A Photoinduced, Benzyne Click Reaction
Gann A.W., Amoroso J.W., Einck V.J., Rice W.P., Chambers J.J., Schnarr N.A.
Organic Letters, 2014
14.
Development and Application of O-(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes
Chen Q., Yu H., Xu Z., Lin L., Jiang X., Wang R.
Journal of Organic Chemistry, 2015
16.
Intramolecular reaction between nitro and carbodi-imide groups; a new synthesis of 2-arylbenzotriazoles
Houghton P.G., Pipe D.F., Rees C.W.
Journal of the Chemical Society Perkin Transactions 1, 1985
18.
W. Fischer, K. Fritzsche, W. Wolf, L. Bore, Patent WO 2002024668 A1, 2002.
20.
Reductive cyclization of o-nitrophenylazobenzenes to 2-aryl-2H-benzotriazoles by SmI2
Kim B.H., Kim S.K., Lee Y.S., Jun Y.M., Baik W., Lee B.M.
Tetrahedron Letters, 1997
23.
A Biphilic Phosphetane Catalyzes N–N Bond-Forming Cadogan Heterocyclization via PIII/PV═O Redox Cycling
Nykaza T.V., Harrison T.S., Ghosh A., Putnik R.A., Radosevich A.T.
Journal of the American Chemical Society, 2017
30.
Reactivity-Based Detection of Copper(II) Ion in Water: Oxidative Cyclization of Azoaromatics as Fluorescence Turn-On Signaling Mechanism
Jo J., Lee H.Y., Liu W., Olasz A., Chen C., Lee D.
Journal of the American Chemical Society, 2012
37.
The chemistry of N-substituted benzotriazoles. Part 1.1-(Chloromethyl)benzotriazole
Katritzky A.R., Rachwal S., Caster K.C., Mahni F., Law K.W., Rubio O.
Journal of the Chemical Society Perkin Transactions 1, 1987
38.
Benzotriazoles. Part 151: The preparation of 1-(1-alkenyl)benzotriazoles
Katritzky A.R., Offerman R.J., Cabildo P., Soleiman M.
Recueil des Travaux Chimiques des Pays-Bas, 2010
41.
Copper in cross-coupling reactions: The post-Ullmann chemistry
Beletskaya I.P., Cheprakov A.V.
Coordination Chemistry Reviews, 2004
44.
Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles
Ueda S., Su M., Buchwald S.L.
Angewandte Chemie - International Edition, 2011
45.
Efficient Synthesis of N-2-Aryl-1,2,3-Triazole Fluorophores via Post-Triazole Arylation
Liu Y., Yan W., Chen Y., Petersen J.L., Shi X.
Organic Letters, 2008
46.
TBAF-Assisted Copper-Catalyzed N-Arylation and Benzylation of Benzazoles with Aryl and Benzyl Halides under the Ligand/Base/ Solvent-Free Conditions
Lee H., Won J., Kim M., Park S., Jung K., Kim B.R., Lee S., Yoon Y.
Journal of Organic Chemistry, 2009
47.
A Concept of Supported Amino Acid Ionic Liquids and Their Application in Metal Scavenging and Heterogeneous Catalysis
Chen W., Zhang Y., Zhu L., Lan J., Xie R., You J.
Journal of the American Chemical Society, 2007
48.
Cu(OAc)2·H2O-catalyzed N-arylation of nitrogen-containing heterocycles
Xu Z., Li H., Ren Z., Du W., Xu W., Lang J.
Tetrahedron, 2011
50.
Deproto-metallation using a mixed lithium–zinc base and computed CH acidity of 1-aryl 1H-benzotriazoles and 1-aryl 1H-indazoles
Nagaradja E., Chevallier F., Roisnel T., Dorcet V., Halauko Y.S., Ivashkevich O.A., Matulis V.E., Mongin F.
Organic and Biomolecular Chemistry, 2014
51.
Mild Copper-Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides
Taillefer M., Ouali A., Renard B., Spindler J.
Chemistry - A European Journal, 2006
53.
Pd- and Cu-catalyzed selective arylation of benzotriazole
Beletskaya I.P., Davydov D.V., Moreno-Mañas M.
Tetrahedron Letters, 1998
54.
Pd- and Cu-catalyzed selective arylation of benzotriazole by diaryliodonium salts in water
Beletskaya I.P., Davydov D.V., Moreno-Mañas M.
Tetrahedron Letters, 1998
58.
10.1016/j.mencom.2018.05.019_bib0105
Albov
Acta Crystallogr., 2004
60.
Unique Bridging Function of the Triazole Core in Copper(II) Chloride Complexes with 1-Allylbenzotriazole
Goreshnik E.A., Schollmeyer D., Mys'kiv M.G.
Zeitschrift fur Anorganische und Allgemeine Chemie, 2005