An efficient one-pot expeditious synthesis of 3-phenyl-1-(6-phenyl-7H-[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazin-3-yl)-1H-pyrazol-5-amines via multicomponent approach

被引:9
|
作者
Sujatha, Kodam [1 ]
Deshpande, Ravindra Pramod [2 ]
Kesharwani, Rajesh Kumar [3 ]
Babu, Phanithi Prakash [2 ]
Vedula, Rajeswar Rao [1 ]
机构
[1] Natl Inst Technol, Dept Chem, Warangal 506004, Telangana, India
[2] Univ Hyderabad, Dept Biotechnol & Bioinformat, Sch Life Sci, Hyderabad, India
[3] Nims Univ Rajasthan, Dept Adv Sci & Technol, NIET, Jaipur, Rajasthan, India
关键词
Multicomponent reaction; phenacyl bromide; 3-(2-bromoacetyl)-2H-chromen-2-one; triazolothiadiazine; TRIAZOLOTHIADIAZINE DERIVATIVES; PYRAZOLE; THIAZOLE; ANALOGS; DESIGN;
D O I
10.1080/00397911.2018.1537398
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of 3-phenyl-1-(6-phenyl-7H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1H-pyrazol-5-amines was accomplished by a simple, atom-economical, and multicomponent approach. Reaction of 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol with various phenacyl bromides and benzoylacetonitriles in ethanol and catalytic amount of acetic acid afforded the titled compounds. The structures of newly synthesized compounds were confirmed by their analytical and spectral (IR, H-1-NMR, C-13-NMR, and Mass) data.
引用
收藏
页码:49 / 55
页数:7
相关论文
共 50 条
  • [21] First Synthesis of the Novel Triazolo[3,4-b][1,3,4]Thiadiazoles and Triazolo[3,4-b][1,3,4]Thiadiazines Linked Chromeno[2,3-b]Pyridine
    Ibrahim, Magdy A. A.
    Al-Harbi, Sami A. A.
    Allehyani, Esam S. S.
    Alqurashi, Esam A. A.
    Alshareef, F. M.
    POLYCYCLIC AROMATIC COMPOUNDS, 2024, 44 (01) : 361 - 374
  • [22] Synthesis and antimicrobial activity of some (3-phenyl-5-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanones: new derivatives of 1,3,5-trisubstituted pyrazolines
    Kumar, Satyender
    Meenakshi
    Kumar, Sunil
    Kumar, Parvin
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (01) : 433 - 439
  • [23] Condensed thiadiazines: Synthesis of [1,2,4]triazino[3,4-b] [1,3,4]thiadiazines
    Heravi, MM
    Rajabzadeh, G
    Rahimizadeh, M
    Bakavoli, M
    Ghassemzadeh, M
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2001, 170 : 205 - 209
  • [24] Synthesis, Crystal Structure and Antiproliferative Activity of 6-Adamantyl-3-aryl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles
    Khan, Mahmood-ul-Hassan
    Akhtar, Tashfeen
    Yasin, Khawaja A.
    Al-Masoudi, Najim A.
    Jones, Peter G.
    Hameed, Shahid
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2010, 65 (02): : 178 - 184
  • [25] Synthesis and antimicrobial activities of novel quinazolin-4(3H)-one derivatives containing a 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole moiety
    Lv, Xinyang
    Yang, Lan
    Fan, Zhijiang
    Bao, Xiaoping
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2018, 22 (01) : 101 - 109
  • [26] Crystal structure of 3,6-diphenyl-7H-[1,2,4]- triazolo[3,4-b][1,3,4]thiadiazine, C16H12N4S
    Ding, Qichun
    Dai, Shudong
    Zhang, Li-Xue
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2018, 233 (05): : 849 - 851
  • [27] Synthesis and anticancer activity of new spirooxindoles incorporating[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine moiety
    Ji, Liangkun
    Zhou, Ying
    Yu, Qiuyan
    Fang, Yaxuan
    Jiang, Yongjun
    Zhao, Yunhui
    Yuan, Chuntao
    Xie, Wenlin
    JOURNAL OF MOLECULAR STRUCTURE, 2021, 1227
  • [28] Synthesis of Some Novel Bis[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine Derivatives for Antimicrobial Evaluation
    Reddy, Cherkupally Sanjeeva
    Rao, Dasari Chandrasekhar
    Yakub, Vookanti
    Nagaraj, Adki
    ACTA CHIMICA SLOVENICA, 2011, 58 (03) : 582 - 589
  • [29] Fused polycyclic nitrogen-containing heterocycles: IX. Synthesis and molecular structure of methyl 3-(2-R-5-phenylthiazol-4-yl)-7-phenyl-7H-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazine-6-carboxylates
    V. A. Mamedov
    L. V. Mustakimova
    A. T. Gubaidullin
    I. A. Litvinov
    Ya. A. Levin
    Russian Journal of Organic Chemistry, 2004, 40 : 1309 - 1317
  • [30] Synthesis and reactions of 3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid
    V. S. Matiichuk
    M. A. Potopnyk
    N. D. Obushak
    Russian Journal of Organic Chemistry, 2009, 45 : 712 - 718