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

被引:968
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
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 41 条
  • [1] ANDERSON N, 2000, PRACTICAL PROCESS RE, pCH4
  • [2] Life in the solar system
    Brack, A
    [J]. LIFE SCIENCES: NEW INSIGHTS INTO COMPLEX ORGANICS IN SPACE, 1999, 24 (04): : 417 - 433
  • [3] Butler R.N., 1996, Comprehensive Heterocyclic Chemistry II, V4
  • [4] tris(2-perfluorohexylethyl) tin azide:: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous organic liquid-liquid extraction
    Curran, DP
    Hadida, S
    Kim, SY
    [J]. TETRAHEDRON, 1999, 55 (29) : 8997 - 9006
  • [5] DUNICA JV, 1991, J ORG CHEM, V56, P2395
  • [6] FEDEROFF BT, 1960, ENCY EXPLOSIVES RELA, V1, pA574
  • [7] FEIGL F, 1975, SPOT TESTS ORGANIC A
  • [8] AN IMPROVED SYNTHESIS OF 5-SUBSTITUTED TETRAZOLES
    FINNEGAN, WG
    HENRY, RA
    LOFQUIST, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (15) : 3908 - 3911
  • [9] FLIPPIN LA, 1991, TETRAHEDRON LETT, V47, P6857
  • [10] Fokin VV, 2001, ANGEW CHEM INT EDIT, V40, P3455, DOI 10.1002/1521-3773(20010917)40:18<3455::AID-ANIE3455>3.0.CO