On Features of Halocyclization of 4-Allyl-5-substituted-2,4-dihydro-3H-1,2,4-triazol-3-thiones and Synthesis of New Derivatives of 1,2,3-Triazoles

被引：1
|
作者：
Galstyan, Armen S. [1 ]
Grigoryan, Sevak V. [1 ]
Samvelyan, Melanya A. [1 ]
Frangyan, Vardges R. [1 ]
Yeganyan, Tigran H. [1 ]
Ayvazyan, Armen G. [2 ]
Ghochikyan, Tariel V. [1 ]
机构：
[1] Yerevan State Univ, Fac Chem, 1 A Manoukyan Str, Yerevan 0025, Armenia
[2] Sci & Technol Ctr Organ & Pharmaceut Chem NAS RA, Mol Struct Res Ctr, 26 Azatutian Ave, Yerevan 0014, Armenia
来源：
CHEMISTRYSELECT | 2022年 / 7卷 / 19期
关键词：
CuAAC reaction; halocyclization; 1; 2; 3-tirazoles; 4-triazole-3-thiones; thiazolo[2; 3-c][1; 4]triazoles; BIOLOGICAL EVALUATION; TRIAZOLE DERIVATIVES; ANTIBACTERIAL; DESIGN;
D O I：
10.1002/slct.202201283
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A study was carried out on the regioselectivity of the electrophilic halocyclization of 4-allyl-5-substituted-2,4-dihydro-3H-1,2,4-triazol-3-thiones by the action of bromine and iodine. It was revealed which factors influence the structure of the reaction products. 6-(Bromomethyl)-3-substituted-5,6-dihydrothiazolo[2,3-c]-[1,2,4]triazoles have been shown to be good starting materials for the synthesis of polyheterocyclic systems containing a 1,2,3-triazole ring. In contrast, 6-iodo-3-substituted-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazines do not undergo azidation. Due to the dehydrohalogenation reaction, a double bond is formed.
引用
收藏
页数：8
相关论文
共 50 条
  • [41] 4-allyl-2-(morpholin-4-ylmethyl)-5-( pyridin-4-yl)2,4-dihydro-3H-1,2,4-triazole-3-thione
    Dinçer, M
    Özdemir, N
    Dege, N
    Çetin, A
    Cansiz, A
    Sekerci, M
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1953 - O1955
  • [42] Comparative QSAR and pharmacophore analysis for a series of 2,4-dihydro-3H-1,2,4-triazol-3-ones derivatives as angiotensin II AT1 receptor antagonists
    Sharma, Mukesh C.
    Sharma, Smita
    Sharma, Pratibha
    Kumar, Ashok
    Bhadoriya, Kamlendra Singh
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (05) : 2486 - 2502
  • [43] Comparative QSAR and pharmacophore analysis for a series of 2,4-dihydro-3H-1,2,4-triazol-3-ones derivatives as angiotensin II AT1 receptor antagonists
    Mukesh C. Sharma
    Smita Sharma
    Pratibha Sharma
    Ashok Kumar
    Kamlendra Singh Bhadoriya
    Medicinal Chemistry Research, 2014, 23 : 2486 - 2502
  • [44] SYNTHESIS OF 3-(2,4-DICHLOROPHENYL)-4-SUBSTITUTED-5-MERCAPTO-1,2,4-TRIAZOLES AND THEIR DERIVATIVES
    GOGOI, PC
    KATAKY, JCS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1990, 29 (12): : 1143 - 1145
  • [45] Crystal packing and molecular dynamics studies of the 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one crystal
    Sorescu, DC
    Thompson, DL
    JOURNAL OF PHYSICAL CHEMISTRY B, 1997, 101 (18): : 3605 - 3613
  • [46] On the possibility for synthesizing dihydrotriazolothiadiazoles by condensation of 4-amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones with aromatic aldehydes
    Bespalov, A. Ya.
    Gorchakova, T. L.
    Ivanov, A. Yu.
    Kuznetsov, M. A.
    Kuznetsova, L. M.
    Pankova, A. S.
    Prokopenko, L. I.
    Khlebnikov, A. F.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (03) : 421 - 428
  • [47] On the possibility for synthesizing dihydrotriazolothiadiazoles by condensation of 4-amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones with aromatic aldehydes
    A. Ya. Bespalov
    T. L. Gorchakova
    A. Yu. Ivanov
    M. A. Kuznetsov
    L. M. Kuznetsova
    A. S. Pankova
    L. I. Prokopenko
    A. F. Khlebnikov
    Russian Journal of Organic Chemistry, 2016, 52 : 421 - 428
  • [48] Azoles .14. 1-substituted 1H-1,2,3-triazoles and 1H-thieno[3,2-d]-1,2,3-triazoles and thieno[3',2':5,6]thiopyrano[2,3-d]-1,2,3-triazoles
    Iddon, B
    Nicholas, M
    JOURNAL OF CHEMICAL RESEARCH-S, 1996, (12): : 512 - &
  • [49] Organocatalytic Selective [3+2] Cycloadditions: Synthesis of Functionalized 5-Arylthiomethy1-1,2,3-triazoles and 4-Arylthio-1,2,3-triazoles
    Reddy, G. Surendra
    Reddy, L. Mallikarjuna
    Kumar, A. Suresh
    Ramachary, Dhevalapally B.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23): : 15488 - 15501
  • [50] Synthesis of 2,4-dihydro-4-(2-phenylethyl)-5-(isomeric pyridyl)-3H-1,2,4-triazole-3-thiones and their derivatives.
    Iqbal, R
    Zamani, K
    Rama, NH
    TURKISH JOURNAL OF CHEMISTRY, 1996, 20 (04): : 295 - 301
12345