Regioselective N1-methylation of 1H-tetrazoles with methyl 2,2,2-trichloroacetimidate

被引:0
|
作者
Baddam, Sudhakar Reddy [1 ]
Kalagara, Sudhakar [2 ]
Ganta, Srinivas [3 ]
Ponnuru, Venkata Suresh [4 ]
Vudari, Balaraju [5 ]
Nalla, Seshadri [6 ]
机构
[1] Univ Massachusetts, Chan Med Sch, RNA Therapeut Inst, Worcester, MA 01655 USA
[2] Univ Texas El Paso, Dept Chem & Biochem, El Paso, TX USA
[3] ScieGen Pharmaceut Inc, Hauppauge, NY USA
[4] Texas Tech Univ, Hlth Sci Pediat Canc Res Ctr, Lubbock, TX USA
[5] Sreenidhi Inst Sci & Technol, Hyderabad, Telangana, India
[6] Cambrex Pharmaceut Co, Charles City, IA USA
关键词
TETRAZOLES; FRAMEWORKS;
D O I
10.1002/jhet.4824
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, mild, and regioselective synthesis of substituted 1-methyl-1H-tetrazole using methyl 2,2,2-trichloroacetimidate is described. The substrate scope of the methodology has been established with wide variety of tetrazoles. N1-Methylated tetrazoles were synthesized with high yields (85%-97%).
引用
收藏
页码:1066 / 1069
页数:4
相关论文
共 50 条
  • [1] Metal-Free Regioselective N2-Arylation of 1H-Tetrazoles with Diaryliodonium Salts
    Saikia, Raktim Abha
    Dutta, Anurag
    Sarma, Bipul
    Thakur, Ashim Jyoti
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 9782 - 9796
  • [2] Regioselective methylation of indazoles using methyl 2,2,2-trichloromethylacetimidate
    Baddam, Sudhakar Reddy
    Kumar, N. Uday
    Reddy, A. Panasa
    Bandichhor, Rakeshwar
    TETRAHEDRON LETTERS, 2013, 54 (13) : 1661 - 1663
  • [3] Sonochemical synthesis of 5-substituted 1H-tetrazoles catalyzed by ZrP2O7 nanoparticles and regioselective conversion into new 2,5-disubstituted tetrazoles
    Safaei-Ghomi, Javad
    Paymard-Samani, Soleiman
    Zahedi, Safura
    Shahbazi-Alavi, Hossein
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2015, 70 (11): : 819 - 828
  • [4] Design, synthesis and pharmacological analysis of 5-[4′-(substituted-methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles
    Kamble, Atulkumar
    Kamble, Ravindra
    Dodamani, Suneel
    Jalalpure, Sunil
    Rasal, Vijaykumar
    Kumbar, Mahadev
    Joshi, Shrinivas
    Dixit, Sheshagiri
    ARCHIVES OF PHARMACAL RESEARCH, 2017, 40 (04) : 444 - 457
  • [5] Design, synthesis and pharmacological analysis of 5-[4′-(substituted-methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles
    Atulkumar Kamble
    Ravindra Kamble
    Suneel Dodamani
    Sunil Jalalpure
    Vijaykumar Rasal
    Mahadev Kumbar
    Shrinivas Joshi
    Sheshagiri Dixit
    Archives of Pharmacal Research, 2017, 40 : 444 - 457
  • [6] Copper-Catalyzed N-tert-Butylation of Aromatic Amines under Mild Conditions Using tert-Butyl 2,2,2-Trichloroacetimidate
    Cran, John W.
    Vidhani, Dinesh V.
    Krafft, Marie E.
    SYNLETT, 2014, 25 (11) : 1550 - 1554
  • [7] Novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors
    Al-Hourani, Baker Jawabrah
    Sharma, Sai Kiran
    Suresh, Mavanur
    Wuest, Frank
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (06) : 2235 - 2238
  • [8] Coupling of N-Tosylhydrazones with Tetrazoles: A Regioselective Synthesis of 2,5-Disubstituted-2H-Tetrazoles
    Kaszas, Timea
    Szakacs, Bence
    Juhasz-Toth, Eva
    Cservenyak, Ivett
    Kovacs, Tamara
    Juhasz, Laszlo
    Somsak, Laszlo
    Toth, Marietta
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (42)
  • [9] 1-(1,2,4-Triazol-3-yl)-1H-tetrazoles and their complexation with copper (II) chloride
    Voitekhovich, Sergei V.
    Grigoriev, Yuri, V
    Lyakhov, Alexander S.
    Matulis, Vadim E.
    Ivashkevich, Ludmila S.
    Bogomyakov, Artem S.
    Lavrenova, Ludmila G.
    Ivashkevich, Oleg A.
    POLYHEDRON, 2020, 176 (176)
  • [10] An Environmentally Friendly Method for N-Methylation of 5-Substituted 1H-Tetrazoles with a Green Methylating Reagent: Dimethyl Carbonate
    Xie, Aming
    Zhang, Qiang
    Liu, Yangyang
    Feng, Liandong
    Hu, Xinyu
    Dong, Wei
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (05) : 1483 - 1487