One-pot synthesis of novel fused mesoionic compounds: 1-substituted-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolin-1-ium-2-thiolates

被引：0
|
作者：
Kovalenko, Sergiy M. [1 ]
Drushlyak, Oleksandr G. [2 ]
Mariutsa, Illia O. [2 ]
机构：
[1] Kharkov Natl Univ, Dept Organ Chem, Kharkiv, Ukraine
[2] Natl Univ Pharm, Fac Pharm, 53 Pushkinska St, UA-61002 Kharkiv, Ukraine
来源：
JOURNAL OF SULFUR CHEMISTRY | 2020年 / 41卷 / 04期
关键词：
Condensation; cyclization; heterocycles; thiols; ylides; BIOLOGICAL EVALUATION; PHARMACOLOGICAL EVALUATION; PARALLEL SYNTHESIS; ANTITUMOR-ACTIVITY; DERIVATIVES; INHIBITORS; RECEPTOR; HETEROCYCLES; ANTICANCER;
D O I：
10.1080/17415993.2020.1742714
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Novel 1-substituted-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolin-1-ium-2-thiolates have been obtained by base catalyzed condensation of methyl 2-isothiocyanatobenzoate with thiosemicarbazides. The reaction occurs via intermediate N-(4-oxo-2-thioxo-1,4-dihydroquinazolin-3(2H)-yl)thioureas followed by cyclization with elimination of the oxygen atom as water and the angular product formation. All new synthesized compounds were fully characterized with elemental and spectroscopic analysis.
引用
收藏
页码：388 / 398
页数：11
相关论文
共 50 条
  • [41] One-Pot, Multi-Component Synthesis of Novel 2-Amino-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide Derivatives as Antiproliferative Agents
    Huo, Xiansen
    Ma, Yufeng
    Chen, Zhiru
    Yuan, Lili
    Zheng, Xiaolan
    Li, Xiongli
    Fengting
    Liang
    You, Wenwei
    Zhao, Peiliang
    CHEMISTRYSELECT, 2021, 6 (18): : 4562 - 4565
  • [42] A Convenient Synthesis of New 2-Phenylthieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine Derivatives by Dimroth Rearrangement
    Son, Hoon Young
    Song, Yang-Heon
    JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2010, 54 (03): : 350 - 353
  • [43] [1,2,4]Triazolo[1,5-d][1,2,4]oxadiazole ring system - A novel building block for creating energetic compounds
    Dou, Hui
    Chen, Peng
    Hu, Lu
    He, Chunlin
    Pang, Siping
    CHEMICAL ENGINEERING JOURNAL, 2022, 444
  • [44] Novel one-pot synthesis of imidazo[2,1-b] [1,2,4]-Triazoles, 1,2,4-Triazolo iminoindoline-2-ones, and their in-vitro antibacterial activity, B-DNA study
    Venkatesham, Papisetti
    Parcha, Sreenivasa Rao
    Rath, Soumya Lipsa
    Chedupaka, Raju
    Vedula, Rajeswar Rao
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (12) : 1989 - 1998
  • [45] Novel variants of the multicomponent reaction for the synthesis of 1,2,4-triazolo[1,5-a]pyrimidines and pyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidines
    Polikarchuk, Vladimir A.
    Chertova, Yuliya V.
    Potapov, Andrei Yu.
    Ledenyova, Irina V.
    Kosheleva, Yevgeniya A.
    Krysin, Mikhail Yu.
    Kozadyorov, Oleg A.
    Shatalov, Gennadiy V.
    Vandyshev, Dmitriy Yu.
    Shikhaliev, Khidmet S.
    Prabhakar, Chetti
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 1054 - 1061
  • [46] Synthesis and energetic properties of trifluoromethyl-substituted 2-nitro-[1,2,4]triazolo[1,5-a]pyrimidine derivatives
    Chinnam, Ajay Kumar
    Staples, Richard J.
    Shreeve, Jean'ne M.
    JOURNAL OF FLUORINE CHEMISTRY, 2021, 245
  • [47] Synthesis and antimicrobial activities of 2-substituted 12H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines, 3-ethoxycarbonyl-12H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-one and ethyl 2-formylamino- and 2-acetylamino-4H-chromene-3-carboxylates
    El-Agrody, Ahmed M.
    Sabry, Nermien M.
    Motlaq, Shymaa S.
    JOURNAL OF CHEMICAL RESEARCH, 2011, (02) : 77 - 83
  • [48] A Convenient One-Pot Synthesis of Thieno[2′,3′:4,5]Pyrimido[1,2-b]-[1,2,4,5]Tetrazines
    Hassan, Allam A.
    Khattab, Reham R.
    Wasfy, Ashraf A. F.
    Abuzeid, Khadiga M.
    Hassan, Nasser A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (04) : 907 - 912
  • [49] An Efficient Three Component One-Pot Synthesis of 5-Amino-7-aryl-7,8-dihydro-[1,2,4] triazolo[4,3-a]-pyrimidine-6-carbonitriles
    Ablajan, Keyume
    Kamil, Wetengul
    Tuoheti, Anagu
    Wan-Fu, Sun
    MOLECULES, 2012, 17 (02) : 1860 - 1869
  • [50] One-Pot Synthesis of 4-Substituted 1H-[1,2,3]triazolo[4,5-c]quinolines Through CuO-Promoted Tandem Cyclization Reactions of (E)-3-(2-Bromoaryl)-1-arylprop-2-en-1-ones with Sodium Azide
    Li, Kangning
    Chen, Jinying
    Li, Jihui
    Chen, Yongxin
    Qu, Jinpeng
    Guo, Xin
    Chen, Chunxia
    Chen, Baohua
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (28) : 6246 - 6248
12345