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
  • [11] Synthesis of some new 5-substituted 1H-tetrazoles
    Disli, A.
    Salman, M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (01) : 151 - 153
  • [12] Efficient Transformation of Inactive Nitriles into 5-Substituted 1H-Tetrazoles Using Microwave Irradiation and Their Applications
    Yoneyama, Hiroki
    Usami, Yoshihide
    Komeda, Seiji
    Harusawa, Shinya
    SYNTHESIS-STUTTGART, 2013, 45 (08): : 1051 - 1059
  • [13] Isolation and crystallographic characterization of a solid precipitate/intermediate in the preparation of 5-substituted 1H-tetrazoles from nitrile in water
    Wang, LZ
    Qu, ZR
    Zhao, H
    Wang, XS
    Xiong, RG
    Xue, ZL
    INORGANIC CHEMISTRY, 2003, 42 (13) : 3969 - 3971
  • [14] An unexpected zinc coordination polymer formed during the preparation of 5-substituted 1H-tetrazoles from a nitrile in water
    Xue, X
    Abrahams, BF
    Xiong, RG
    You, XZ
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2002, 55 (08) : 495 - 497
  • [15] MICROWAVE SYNTHESIS OF 5-SUBSTITUTED 1H-TETRAZOLES CATALYZED BY BISMUTH CHLORIDE IN WATER
    Coca, Adiel
    Feinn, Liana
    Dudley, Joshua
    SYNTHETIC COMMUNICATIONS, 2015, 45 (08) : 1023 - 1030
  • [16] An efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by graphene
    Qi, Gang
    Zhang, Wenguo
    Dai, Yong
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (02) : 1149 - 1155
  • [17] Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles
    Patil, Dipak R.
    Deshmukh, Mukesh B.
    Dalal, Dipak S.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2012, 9 (05) : 799 - 803
  • [18] The synthesis of 5-substituted 1H-tetrazoles in molten tetrabutylammonium bromide
    Xie, Aming
    Cao, Meiping
    Feng, Liandong
    Dong, Wei
    JOURNAL OF CHEMICAL RESEARCH, 2013, (11) : 665 - 667
  • [19] Iron Salts in the Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles
    Bonnamour, Julien
    Bolm, Carsten
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (18) : 4543 - 4545
  • [20] An efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by graphene
    Gang Qi
    Wenguo Zhang
    Yong Dai
    Research on Chemical Intermediates, 2015, 41 : 1149 - 1155
12345