N1-, N2-, and N3-Methyl-4-nitro-1,2,3-triazoles and Metal Complexes Based on Them

被引:0
作者
Filippova, Yu. V. [1 ]
Krupnova, I. A. [1 ]
Bosov, K. K. [1 ]
Sukhanov, G. T. [1 ]
Sukhanova, A. G. [1 ]
Pivovarova, E. V. [1 ]
机构
[1] Russian Acad Sci, Inst Problems Chem & Energet Technol, Siberian Branch, Biisk 659322, Altai Krai, Russia
关键词
nitrotriazole; alkylation; regioselectivity; N-methylnitrotriazoles; coordination compounds; ALKYLATION; TRIAZOLES;
D O I
10.1134/S1070427223030114
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Alkylation of an NH-heterocycle, 4-nitro-1,2,3-triazole, with dimethyl sulfate is accompanied by tandem alkylation-quaternization and yields a complex mixture of products of N-monoalkylation at all the three heteroatoms, N-1, N-2, and N-3, with the significant prevalence of the N3 derivative and product of its further transformation, 1,3-dimethyl-4-nitro-1,2,3-triazolium salt. Previously unknown complexes of N3-methylnitrotriazole with copper(II) and nickel(II) ions were prepared.
引用
收藏
页码:366 / 371
页数:6
相关论文
共 11 条
[1]  
Abboud JLM, 2001, EUR J ORG CHEM, V2001, P3013
[2]   Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].
Agalave, Sandip G. ;
Maujan, Suleman R. ;
Pore, Vandana S. .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718
[3]   Triazoles and tetrazoles: Prime ligands to generate remarkable coordination materials [J].
Aromi, Guillem ;
Barrios, Leoni A. ;
Roubeau, Olivier ;
Gamez, Patrick .
COORDINATION CHEMISTRY REVIEWS, 2011, 255 (5-6) :485-546
[4]  
Baryshnikov A.T., 1992, Russ. Chem. Bull., V41, P751, DOI [10.1007/bf01150904, DOI 10.1007/BF01150904]
[5]   1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview [J].
Bozorov, Khurshed ;
Zhao, Jiangyu ;
Aisa, Haji A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) :3511-3531
[6]   Acid Catalyzed tert-Butylation and Tritylation of 4-Nitro-1,2,3-triazole: Selective Synthesis of 1-Methyl-5-nitro-1,2,3-triazole via 1-tert-Butyl-4-nitro-1,2,3-triazole [J].
Filippova, Yuliya V. ;
Sukhanova, Anna G. ;
Voitekhovich, Sergei V. ;
Matulis, Vadim E. ;
Sukhanov, Gennady T. ;
Grigoriev, Yury V. ;
Ivashkevich, Oleg A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) :965-968
[7]   Quantum-chemical investigation of certain physicochemical properties of C-nitro-1,2,3-triazole and N-alkyl-4(5)-nitro-1,2,3-triazoles [J].
Ivashkevich, O. A. ;
Matulis, Vadim E. ;
Gaponik, P. N. ;
Sukhanov, G. T. ;
Filippova, J. V. ;
Sukhanova, A. G. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (12) :1472-1482
[8]   Complete basis set calculations on the tautomerism and protonation of triazoles and tetrazole [J].
Jimenez, Veronica ;
Alderete, Joel B. .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2006, 775 (1-3) :1-7
[9]   Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in strongly acidic media [J].
Sakovich, G. V. ;
Sukhanov, G. T. ;
Filippova, Yu V. ;
Sukhanova, A. G. ;
Bosov, K. K. .
RUSSIAN CHEMICAL BULLETIN, 2013, 62 (01) :111-116
[10]   Regioselective quaternization of N-alkyl-4-nitro-1,2,3-triazoles in ButOH-HClO4 system [J].
Sukhanov, Gennady T. ;
Sakovich, Gennady V. ;
Filippova, Yulia V. ;
Bagryanskaya, Irina Yu ;
Sukhanova, Anna G. .
MENDELEEV COMMUNICATIONS, 2014, 24 (05) :280-282