The synthesis of phosphaisocoumarins by Cu(I)-catalyzed intramolecular cyclization of o-ethynylphenylphosphonic acid monoesters

被引:95
作者
Peng, AY [1 ]
Ding, YX [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ja038627f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cu(I)-catalyzed intramolecular cyclization of o-ethynylphenylphosphonic acid monoethyl esters was examined, and a new class of six-membered phosphorus heterocycles was formed with high regioselectivity and good yields. The present reaction is the first example of intramolecular addition of P?OH to alkynes, which provides a convenient way to synthesize novel phosphorus heterocycles having potential bioactivities. Copyright © 2003 American Chemical Society.
引用
收藏
页码:15006 / 15007
页数:2
相关论文
共 45 条
  • [21] SYNTHESIS OF ISOCOUMARINS FROM O-IODOBENZOIC ACID AND TERMINAL ACETYLENES MEDIATED BY PALLADIUM COMPLEXES AND ZINC-CHLORIDE
    LIAO, HY
    CHENG, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) : 3711 - 3716
  • [22] Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction
    Ma, CR
    Liu, XX
    Li, XY
    Flippen-Anderson, J
    Yu, S
    Cook, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) : 4525 - 4542
  • [23] Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization
    McDonald, FE
    Reddy, KS
    Díaz, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) : 4304 - 4309
  • [24] Group VI metal-promoted endo-azacyclizations via alkyne-derived metal vinylidene carbenes
    McDonald, FE
    Chatterjee, AK
    [J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7687 - 7690
  • [25] Melis K, 2002, EUR J ORG CHEM, V2002, P3779
  • [26] Palladium-catalyzed cyclization of 6-aminohex-1-yne
    Müller, TE
    Berger, M
    Grosche, M
    Herdtweck, E
    Schmidtchen, FP
    [J]. ORGANOMETALLICS, 2001, 20 (21) : 4384 - 4393
  • [27] NOZAWA K, 1981, CHEM PHARM BULL, V29, P2491
  • [28] OGAWA Y, 1995, HETEROCYCLES, V41, P2587
  • [29] Peng AY, 2003, SYNTHESIS-STUTTGART, P205
  • [30] Irreversible inhibitors of serine, cysteine, and threonine proteases
    Powers, JC
    Asgian, JL
    Ekici, ÖD
    James, KE
    [J]. CHEMICAL REVIEWS, 2002, 102 (12) : 4639 - 4750