A Mild and Highly Efficient Method for the Synthesis of 5-Aryl-(N-phenyl-)6H-1,3,4-thiadiazin-2-aminium Salts Using Reusable Heterogeneous Catalysts

被引:7
|
作者
Rostamizadeh, Shahnaz [1 ]
Shadjou, Nasrin [1 ]
Amani, Ali M. [1 ]
Aryan, Reza [1 ]
机构
[1] KN Toosi Univ Technol, Dept Chem, Tehran, Iran
关键词
D O I
10.1002/jhet.5570450631
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Aryl-6H-1,3,4-thiadiazin-2-aminium and 5-aryl-N-phenyl-6H-1,3,4-thiadiazin-2-aminium salts have efficiently been synthesized from the reaction of thiosemicarbazide and alpha-haloketones in acetonitrile at room temperature using i) silica supported sodium hydrogen sulfate and ii) silica sulfuric acid as reusable heterogeneous catalysts. The experimental procedure is simple and the products are obtained in high yields.
引用
收藏
页码:1761 / 1764
页数:4
相关论文
共 17 条
  • [1] 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
    Sujatha, Kodam
    Deshpande, Ravindra Pramod
    Kesharwani, Rajesh Kumar
    Babu, Phanithi Prakash
    Vedula, Rajeswar Rao
    SYNTHETIC COMMUNICATIONS, 2019, 49 (01) : 49 - 55
  • [2] Polyaniline salts and complexes: Efficient and reusable catalyst for the one-pot synthesis of 5-(methoxycarbonyl)-6-methyl-4-phenyl-3, 4-dihydropyrimidin-2(1H)-one
    Gangadasu, Banda
    Palaniappan, Srinivasan
    Amarnath, Chellachamy Anbalagan
    Rao, Vaidya Jayathirtha
    Journal of Applied Polymer Science, 2006, 102 (02): : 1741 - 1745
  • [3] Polyaniline salts and complexes: Efficient and reusable catalyst for the one-pot synthesis of 5-(methoxycarbonyl)-6-methyl-4-phenyl-3, 4-dihydropyrimidin-2(1H)-one
    Gangadasu, Banda
    Palaniappan, Srinivasan
    Amarnath, Chellachainy Anbalagan
    Rao, Vaidya Jayathirtha
    JOURNAL OF APPLIED POLYMER SCIENCE, 2006, 102 (02) : 1741 - 1745
  • [4] SYNTHESES WITH ALKENEDIAZONIUM SALTS .6. 2,2-DIETHOXY-1-ETHENEDIAZONIUM HEXACHLOROANTIMONATE - A VERSATILE BUILDING BLOCK FOR THE SYNTHESIS OF 5-MEMBERED AND 6-MEMBERED N-HETEROCYCLES CRYSTAL AND MOLECULAR-STRUCTURE OF 5'-PHENYL-3'-(2-PHENYL-6H-1,3,4-OXADIAZINE-5-YL)SPIRO[ISOBENZOFURAN-1(3H),2'(3'H)-[1,3,4]-OXADIAZOL]-3-ONE[1]
    SAALFRANK, RW
    WEISS, B
    WIRTH, U
    PETERS, K
    VONSCHNERING, HG
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1989, 44 (05): : 587 - 597
  • [5] SYNTHESIS OF 2,3-DIHYDRO-3-AMINO-6-PHENYL-2-THIOXOTHIENO[2,3-D]PYRIMIDIN-4(1H)-ONE AND OF POTENTIAL ANTIINFLAMMATORY AGENTS 2-ARYL-7-PHENYL-3H,9H-PYRIMIDO[2,1-B]THIENO[2',3',4,5][1,3,4]THIADIAZIN-9-ONES
    SANTAGATI, A
    MODICA, M
    SANTAGATI, M
    CARUSO, A
    CUTULI, V
    PHARMAZIE, 1994, 49 (01): : 64 - 65
  • [6] Synthesis and crystal structure of ((6R,7S)-3-ethyl-6-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)(phenyl)methanone hemihydrate, 2(C19H18N4OS) • H2O
    Ding, Qichun
    Yang, Ruya
    Yao, Peipao
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2020, 235 (05): : 1157 - 1159
  • [7] Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′′(chloro-aryl-methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition
    Debnath, Kamalesh
    Pathak, Sudipta
    Pramanik, Animesh
    TETRAHEDRON LETTERS, 2013, 54 (08) : 896 - 899
  • [8] Synthesis, Characterization, and Antimicrobial Activity of a Series of 2-(5-Phenyl-1,3,4-oxadiazol-2-yl)-N-[(1-aryl-1H-1,2,3-triazol-4-yl)methyl]anilines Using Click Chemistry
    Venkatagiri, N.
    Krishna, T.
    Thirupathi, P.
    Bhavani, K.
    Reddy, C. K.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (07) : 1488 - 1494
  • [9] Synthesis, Characterization, and Antimicrobial Activity of a Series of 2-(5-Phenyl-1,3,4-oxadiazol-2-yl)-N-[(1-aryl-1H-1,2,3-triazol-4-yl)methyl]anilines Using Click Chemistry
    N. Venkatagiri
    T. Krishna
    P. Thirupathi
    K. Bhavani
    C. K. Reddy
    Russian Journal of General Chemistry, 2018, 88 : 1488 - 1494
  • [10] A clean and highly efficient synthesis of 4,4′-(arylmethylene) bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) using Ce(SO4)2.4H2O as heterogeneous catalyst
    Mosaddegh, Elaheh
    Islami, Mohammad Reza
    Shojaie, Zohreh
    ARABIAN JOURNAL OF CHEMISTRY, 2017, 10 : S1200 - S1203