An intramolecular [2+3] cycloaddition route to fused 5-heterosubstituted tetrazoles

被引:285
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/ol010220x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Fused 5-heterotetrazole ring systems are synthesized in high yield via intramolecular [2 + 3] cycloadditions of organic azides and heteroatom-substituted nitriles. Cyanates, thiocyanates, and cyanamides are all competent dipolarophiles for this reaction. A variety of scaffolds are tolerated when the new enclosed ring is five- or six-membered.
引用
收藏
页码:4091 / 4094
页数:4
相关论文
共 30 条
  • [11] TETRAZOLO[1,5-B]-1,2,4-TRIAZINES - SYNTHESES AND STRUCTURE DETERMINATION
    GOODMAN, MM
    ATWOOD, JL
    CARLIN, R
    HUNTER, W
    PAUDLER, WW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (17) : 2860 - 2864
  • [12] JENSEN KA, 1964, ACTA CHEM SCAND, V18, P826, DOI 10.3891/acta.chem.scand.18-0826
  • [13] ALKYL CYANATES .3. PREPARATION AND PROPERTIES OF ALKYL CYANATES
    JENSEN, KA
    DUE, M
    HOLM, A
    [J]. ACTA CHEMICA SCANDINAVICA, 1965, 19 (02): : 438 - &
  • [14] ROLE OF PROTIC AND DIPOLAR APROTIC-SOLVENTS IN CYCLOADDITION REACTIONS INVOLVING ANIONIC 1,3-DIPOLES - ACTION OF INORGANIC AZIDES ON IMIDOYL CHLORIDES
    KADABA, PK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (06) : 1073 - 1075
  • [15] KATNER AS, 1974, Patent No. 3962272
  • [16] Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO
  • [17] 2-5
  • [18] KRANTZ A, 1975, TETRAHEDRON LETT, V9, P695
  • [19] KRAYUSHIN MM, 1980, IAN SSSR KH, V11, P2668
  • [20] Lwowski W., 1984, 1 3 DIPOLAR CYCLOADD, V1, P559