1-Substituted 5-Aminotetrazoles: Syntheses from CNN3 with Primary Amines

被引:83
|
作者
Joo, Young-Hyuk [1 ]
Shreeve, Jean'ne M. [1 ]
机构
[1] Univ Idaho, Dept Chem, Moscow, ID 83844 USA
关键词
D O I
10.1021/ol8019742
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Substituted 5-aminotetrazoles were prepared in situ by an excellent reaction of cyanogen azide and primary amines to generate an imidoyl azide as an intermediate in acetonitrile/water. After cyclization, the intermediate gave 1-substituted aminotetrazole in good yield. This protocol also was utilized in the syntheses of bis- and tris(1-substituted 5-aminotetrazole) derivatives.
引用
收藏
页码:4665 / 4667
页数:3
相关论文
共 50 条
  • [21] Studies with heteroaromatic amines: The reaction of some heteroaromatic amines with 1-substituted 3-dimethylaminopropanones, enaminones and cinnamonitriles
    AlEnezi, A
    AlSaleh, B
    Elnagdi, MH
    JOURNAL OF CHEMICAL RESEARCH-S, 1997, (01): : 4 - &
  • [23] ELECTRON-SPIN RESONANCE STUDY OF RADICALS FORMED BY GAMMA-IRRADIATION OF 1-SUBSTITUTED 5-NITRO-AMINO AND 5-NITROSO-AMINOTETRAZOLES
    CATTON, RC
    BUTLER, RN
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (08): : 1248 - 1252
  • [24] CD .94. CD OF PRIMARY AMINES AND 1-SUBSTITUTED OR 3-SUBSTITUTED TETRAHYDROISOQUINOLINES IN PRESENCE OF [RH2(O2CCH3)4]
    DIENER, W
    FRELEK, J
    SNATZKE, G
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (05) : 954 - 965
  • [25] QUALITATIVE REACTION OF 1-SUBSTITUTED TETRAZOLINE-5-THIONES WITH BISMUTH (3)
    JOHAR, GS
    AGARWALA, U
    CURRENT SCIENCE, 1969, 38 (20): : 492 - &
  • [26] PYRAZOLONE DERIVATIVES .8. SYNTHESES OF 1-SUBSTITUTED 4-ARYLHYDRAZONO-3-METHYL-2-PYRAZOLIN-5-ONES AND 1-SUBSTITUTED 4-ARYLAZO-3,5-DIMETHYLPYRAZOLES AS POTENTIAL ANTIINFLAMMATORY AGENTS
    ISMAIEL, AM
    YOUSIF, MY
    METWALLY, MA
    ELKERDAWY, M
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (12): : 1238 - 1242
  • [27] A Facile One-Pot Synthesis of 1-Substituted Tetrazole-5-thiones and 1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles from Organic Isothiocyanates
    Han, Sam Yong
    Lee, Je Woo
    Kim, Hee-Jung
    Kim, Yong-Joo
    Lee, Soon W.
    Gyoung, Young Soo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (01): : 55 - 59
  • [28] Syntheses of 1-substituted furan-fused 3-sulfolenes and their Diels-Alder reactions
    Suzuki, T
    Fuchii, H
    Takayama, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (22): : 2699 - 2704
  • [29] A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton
    Archibald, Glenn
    Lin, Chih-Pei
    Boyd, Peter
    Barker, David
    Caprio, Vittorio
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18): : 7968 - 7980