Preparation of 5-substituted 1H-tetrazoles from nitriles in water

被引：969
|
作者：
Demko, ZP
Sharpless, KB
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 24期
关键词：
D O I：
10.1021/jo010635w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.
引用
收藏
页码：7945 / 7950
页数：6
相关论文
共 50 条
  • [21] Alkylation of 5-substituted 1H-tetrazoles using the Mitsunobu reaction
    Kumar, Sunil
    Coca, Adiel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [22] Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles
    Dipak R. Patil
    Mukesh B. Deshmukh
    Dipak S. Dalal
    Journal of the Iranian Chemical Society, 2012, 9 : 799 - 803
  • [23] Synthesis of 5-Substituted 1H-Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate
    Ishihara, Kotaro
    Kawashima, Mayumi
    Shioiri, Takayuki
    Matsugi, Masato
    SYNLETT, 2016, 27 (15) : 2225 - 2228
  • [24] Facile Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by Tetrabutylammonium Hydrogen Sulfate in Water
    Wang, Zengtao
    Liu, Zhiguo
    Cheon, Seung Hoon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01) : 198 - 202
  • [25] Synthesis of 5-substituted 1H-tetrazoles in water catalyzed by rare-earth metals
    Feinn, Liana
    Coca, Adiel
    Turek, Evan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [26] A Magnetically Recoverable and Reusable Catalyst for Synthesis of 5-Substituted 1H-Tetrazoles
    Elhampour, Ali
    Nemati, Firouzeh
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2018, 50 (05) : 493 - 501
  • [27] Alkylation of 5-Substituted 1H-Tetrazoles via the Diazotization of Aliphatic Amines
    Reynard, Guillaume
    Lebel, Helene
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17): : 12452 - 12459
  • [28] Syntheses of 5-Substituted 1H-Tetrazoles Catalyzed by Reusable CoY Zeolite
    Rama, Velladurai
    Kanagaraj, Kuppusamy
    Pitchumani, Kasi
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 9090 - 9095
  • [29] Tungstates: Novel heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles
    He, Jinghui
    Li, Baojun
    Chen, Fasheng
    Xu, Zheng
    Yin, Gui
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2009, 304 (1-2) : 135 - 138
  • [30] Synthesis of 5-substituted 1H-tetrazoles catalyzed by ytterbium triflate hydrate
    Turek, Evan
    Coca, Adiel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
12345