Addition of carbon nucleophiles to aldehyde tosylhydrazones of aromatic and heteroaromatic-compounds: total synthesis of piperine and its analogs

被引:20
作者
Chandrasekhar, S [1 ]
Reddy, MV [1 ]
Reddy, KS [1 ]
Ramarao, C [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
关键词
toluene-p-sulphonylhydrazine; piperine; anti-feedant; insecticide;
D O I
10.1016/S0040-4039(00)00219-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of carbon nucleophiles to aldehyde tosylhydrazones of aromatic and heteroaromatic compounds is reported. New observations have been made wherein alkylative reduction is observed in some cases whereas alkylative fragmentation is noticed in others. These findings are exploited in the synthesis of the useful alkaloid piperine and its analogs. (C) 2000 EIsevier Science Ltd. All rights reserved.
引用
收藏
页码:2667 / 2670
页数:4
相关论文
共 15 条
  • [1] RECENT APPLICATIONS OF THE SHAPIRO REACTION
    ADLINGTON, RM
    BARRETT, AGM
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) : 55 - 59
  • [2] [Anonymous], 1976, Org. React
  • [3] BALKRISHNA SB, 1981, TETRAHEDRON, V37, P2091
  • [4] Chamberlin A.R., 1990, Org. React, V39, P1
  • [5] Caveat in alkylative fragmentation of aldehyde tosylhydrazones of cyclic ethers
    Chandrasekhar, S
    Reddy, MV
    Takhi, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (36) : 6535 - 6538
  • [6] ALKYLATIVE ELIMINATION OF ALPHA,BETA-EPOXY TOSYLHYDRAZONES
    CHANDRASEKHAR, S
    TAKHI, M
    YADAV, JS
    [J]. TETRAHEDRON LETTERS, 1995, 36 (02) : 307 - 310
  • [7] CHANDRASEKHAR S, 1995, TETRAHEDRON LETT, V36, P5071
  • [8] CHANDRASEKHAR S, 1996, TETRAHEDRON LETT, V37, P759
  • [9] ALKALOIDS OF PIPER LONGUM LINN .I. STRUCTURE AND SYNTHESIS OF PIPERLONGUMINE AND PIPERLONGUMININE
    CHATTERJEE, A
    DUTTA, CP
    [J]. TETRAHEDRON, 1967, 23 (04) : 1769 - +
  • [10] Kumar P, 1998, SYNTHESIS-STUTTGART, P33