[4+2] Cycloaddition Reactions Between 1,8-Disubstituted Cyclooctatetraenes and Diazo Dienophiles: Stereoelectronic Effects, Anticancer Properties and Application to the Synthesis of 7,8-Substituted Bicyclo[4.2.0] octa-2,4-dienes

被引：8
作者：
Grange, Rebecca L. [1 ]
Gallen, Michael J. [1 ]
Schill, Heiko [1 ]
Johns, Jenny P. [2 ]
Dong, Lin [1 ]
Parsons, Peter G. [2 ]
Reddell, Paul W. [3 ]
Gordon, Victoria A. [3 ]
Bernhardt, Paul V. [1 ]
Williams, Craig M. [1 ]
机构：
[1] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia
[2] PO Royal Brisbane Hosp, Queensland Inst Med Res, Brisbane, Qld 4029, Australia
[3] EcoBiotics Ltd, Yungaburra, Qld 4884, Australia
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 29期
关键词：
antitumor agents; bicyclo compounds; cycloaddition; cyclooctatetraene; diazo compounds; Diels-Alder reaction; ENDIANDRA-INTRORSA LAURACEAE; A-ACID-G; BIOMIMETIC SYNTHESIS; ORGANIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ORTHO-PHOTOCYCLOADDITION; VALENCE ISOMERIZATION; STEROIDAL 5,7-DIENES; RETRO-CYCLOADDITION; CYCLO-OCTATETRAENES;
D O I：
10.1002/chem.200903454
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A detailed examination of [4+2] cycloaddition reactions between 1,8-disubstituted cyclooctatetraenes and diazo compounds revealed that 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) reacts to form either 2,3- or 3.4-disubstituted adducts. The product distribution can be controlled by modulating the electron density of the cyclooctatetraene. Unprecedented [4+2] cycloadditions between diisopropyl azodicarboxylate (DIAD) and 1,8-disubstituted cyclooctatetraenes are also described and further manipulation of a resulting cycloadduct uncovered a new pathway to the synthetically challenging bicyclo[4.2.0]octa-2,4-diene family. Variation of the substituents resulted in a range of compounds displaying selective action against different human tumour cell types.
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收藏
页码：8894 / 8903
页数：10
相关论文
共 145 条
  • [1] POLYCYCLIC ARYLPIPERAZINYL AND HETEROARYLPIPERAZINYL IMIDES AS 5-HT1A RECEPTOR LIGANDS AND POTENTIAL ANXIOLYTIC AGENTS - SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP STUDIES
    ABOUGHARBIA, M
    PATEL, UR
    WEBB, MB
    MOYER, JA
    ANDREE, TH
    MUTH, EA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (07) : 1382 - 1392
  • [2] SYNTHESIS AND STRUCTURE ACTIVITY RELATIONSHIP OF SUBSTITUTED TETRAHYDRO AND HEXAHYDRO-1,2-BENZISOTHIAZOL-3-ONE 1,1-DIOXIDES AND THIADIAZINONES - POTENTIAL ANXIOLYTIC AGENTS
    ABOUGHARBIA, M
    MOYER, JA
    PATEL, U
    WEBB, M
    SCHIEHSER, G
    ANDREE, T
    HASKINS, JT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (05) : 1024 - 1033
  • [3] SYNTHESIS OF THE ENDOPEROXIDE ANTI-7,8-DIOXATRICYCLO[4.2.2.02,5]DECA-3,9-DIENE VIA SINGLET OXYGENATION OF THE BICYCLIC VALENCE TAUTOMER OF CYCLOOCTATETRAENE AND ITS TRANSFORMATIONS
    ADAM, W
    CUETO, O
    DELUCCHI, O
    PETERS, K
    PETERS, EM
    VONSCHNERING, HG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (19) : 5822 - 5828
  • [4] CYCLOADDITION OF SINGLET OXYGEN AND "4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE (MTAD) TO METHOXYCYCLOOCTATETRAENE (MCOT)
    ADAM, W
    KLUG, G
    SCHEUTZOW, D
    PETERS, K
    PETERS, EM
    VONSCHNERING, HG
    [J]. TETRAHEDRON LETTERS, 1982, 23 (28) : 2837 - 2840
  • [5] SYNTHESIS OF ENDOPEROXIDES DERIVED FROM CYCLOOCTATETRAENES VIA SINGLET OXYGENATION
    ADAM, W
    KLUG, G
    PETERS, EM
    PETERS, K
    VONSCHNERING, HG
    [J]. TETRAHEDRON, 1985, 41 (11) : 2045 - 2056
  • [6] Iodine assisted palladium catalyzed ring opening of bicyclic hydrazines with organoboronic acids: stereoselective synthesis of functionalized cyclopentenes and alkylidene cyclopentenes
    Anas, S.
    John, Jubi
    Sajisha, V. S.
    John, Joshni
    Rajan, Rani
    Suresh, E.
    Radhakrishnan, K. V.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (24) : 4010 - 4019
  • [7] STUDIES OF CHROMENES .4. OXIDATION OF HEXAHYDRO-5H-CHROMENO[3,4-C]-PYRIDAZINES AND CONFORMATIONAL ISOMERISM IN TETRA AND HEXA-HYDRO-N,N'-DIALKOXYCARBONYL-5H-CHROMENO[3,4-C]PYRIDAZINES
    ANASTASIS, P
    BROWN, PE
    MARCUS, WY
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12): : 2815 - 2825
  • [8] SYNTHESES, SPECTRA, AND SOME REACTIONS OF 2-PHTHALIMIDYL AND 2-PHTHALIMIDYL-4,5-DICHLORO-5-AZABICYCLO[2.1.0]PENTANE
    ANDERSON, AG
    FAGERBUR.DR
    [J]. TETRAHEDRON, 1973, 29 (19) : 2973 - 2979
  • [9] ANET R, 1961, TETRAHEDRON LETT, P720
  • [10] SYNTHESIS AND CHEMISTRY OF BICYCLO[4.2.1]NONA-2,4,7-TRIEN-9-ONE AND OF "BICYCLO[4.2.1]NONA-2,4,7-TRIEN-9-YL INTERMEDIATES
    ANTKOWIA.TA
    SHECHTER, H
    TRIMITSI.GB
    SANDERS, DC
    PRESS, JB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) : 5366 - &
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