Synthetic Strategy and Structure Characterization of a New [1,3]Thiazolo[3,2-b][1,2,4]Triazolium Cationic Surfactant

被引：7
|
作者：
Fizer, Maksym [1 ]
Slivka, Mikhailo [1 ]
Fizer, Oksana [1 ]
机构：
[1] Uzhgorod Natl Univ, Fac Chem, Dept Organ Chem, Fedinets Str 53-1, UA-88000 Uzhgorod, Ukraine
来源：
BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY | 2021年 / 11卷 / 06期
关键词：
1,2,4-triazole; alkylation; cyclization; surfactant; NMR; cation; PM7; semiempirical;
D O I：
10.33263/BRIAC116.1388513892
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Here, we present a synthetic strategy to access a new [1,3]thiazolo[3,2-b][1,2,4]triazolium-based cationic surfactant via the use of proton-induced heterocyclization method for quaternization of a nitrogen atom. The two-step synthesis of 2-heptyl-6,6-dimethyl-3-phenyl-5,6-dihydro-3H-[1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium perchlorate is described in details. The analysis of NMR spectra unequivocally proved the formation of the 1,3-thiazolinium ring upon cyclization reaction. PM7 semiempirical calculations testify to the similar electronic structure of the newly synthesized surfactant cation and 1-heptylpyridinium cation.
引用
收藏
页码：13885 / 13892
页数：8
相关论文
共 50 条
  • [21] Synthesis of New Thiazolo[3,2-b][1,2,4]triazole Derivatives and Preliminary Evaluation of Their Biological Activity
    A. P. Yengoyan
    V. A. Pivazyan
    E. A. Chazaryan
    R. S. Hakobyan
    Russian Journal of General Chemistry, 2019, 89 : 32 - 36
  • [22] Synthesis of New Thiazolo[3,2-b][1,2,4]triazole Derivatives and Preliminary Evaluation of Their Biological Activity
    Yengoyan, A. P.
    Pivazyan, V. A.
    Chazaryan, E. A.
    Hakobyan, R. S.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (01) : 32 - 36
  • [23] [1,3]Oxazolo[3,2-b][1,2,4]triazoles: a versatile synthesis of a novel heterocycle
    Ball, Catherine
    Dean, David K.
    Lorthioir, Olivier
    Page, Lee W.
    Smith, Charlotte L.
    Watson, Stephen P.
    TETRAHEDRON LETTERS, 2010, 51 (30) : 3907 - 3909
  • [24] Structure of reaction products of substituted [1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-ones with amines and hydrazines
    Rzhevskii, A. A.
    Gerasimova, N. P.
    Chirkova, Zh. V.
    Filimonov, S. I.
    Firgang, S. I.
    Stashina, G. A.
    Suponitsky, K. Yu.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (11) : 1680 - 1685
  • [25] Structure of reaction products of substituted [1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-ones with amines and hydrazines
    A. A. Rzhevskii
    N. P. Gerasimova
    Zh. V. Chirkova
    S. I. Filimonov
    S. I. Firgang
    G. A. Stashina
    K. Yu. Suponitsky
    Russian Journal of Organic Chemistry, 2013, 49 : 1680 - 1685
  • [26] Ultrasound promoted green synthesis of benzofuran substituted thiazolo[3,2-b][1,2,4] triazoles
    Kumar, Surender
    Sharma, Dinesh Kumar
    GREEN PROCESSING AND SYNTHESIS, 2017, 6 (01) : 73 - 77
  • [27] Anti-Inflammatory, Radical Scavenging Mechanism of New 4-Aryl-[1,3]-thiazol-2-yl-2-quinoline Carbohydrazides and Quinolinyl[1,3]-thiazolo[3,2-b][1,2,4]triazoles
    Srinivasa, Shashidhar Bharadwaj
    Poojary, Boja
    Brahmavara, Usha
    Das, Anupam Jyoti
    Middha, Sushil Kumar
    CHEMISTRYSELECT, 2018, 3 (44): : 12478 - 12485
  • [28] SYNTHESIS OF [1,3]THIAZOLO[3,2-B]-S-TRIAZOLES AND [1,3]THIAZOLO[2,3-C]-S-TRIAZOLES
    MIGNOT, A
    MOSKOWITZ, H
    MIOCQUE, M
    SYNTHESIS-STUTTGART, 1979, (01): : 52 - 53
  • [29] Deuterium studies in the cyclization and isomerization of 3-propargylmercapto-1,2,4-triazines to thiazolo[3,2-b]-[1,2,4] triazines
    Heravi, MM
    Shafaie, M
    Khosrofar, P
    Ghassemzdeh, M
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 167 : 21 - 27
  • [30] Synthesis of benzothiazolo[3,2-b][1,2,4]triazepines
    Gupta, SB
    Gakhar, HK
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 7 (02) : 157 - 158
12345