STUDIES OF CHROMENES .10. OXIRANES OF NITROCHROMENES

被引:26
作者
BROWN, PE
LEWIS, RA
机构
[1] Department of Chemistry, The University
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 05期
关键词
D O I
10.1039/p19920000573
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of stable oxiranes of 5- and 7-nitro-, and 5,7-dinitro- 2,2-dimethyl(chromenes and of 7-2H-ethoxycarbonylamino)-2,2-dimethyl-5-nitro-2H-chromene are described. Thermal cyclisation of the precursor phenyl prop-2-ynyl ethers proceeds in good yield but in the case of the dinitrophenyl ether the products are highly solvent dependent. The compounds are of interest as possible antitumour alkylating agents that are activated by bioreduction to extremely reactive oxiranes.
引用
收藏
页码:573 / 577
页数:5
相关论文
共 26 条
  • [1] THERMAL-BEHAVIOR OF ARYL GAMMA-HALOPROPARGYL ETHERS
    ARIAMALA, G
    BALASUBRAMANIAN, KK
    [J]. TETRAHEDRON, 1989, 45 (01) : 309 - 318
  • [2] ARNONE A, 1967, TETRAHEDRON LETT, V43, P4201
  • [3] BRANDSMA L, 1970, RECL TRAV CHIM PAY-B, V89, P110
  • [4] BRANDSMA L, 1969, RECL TRAV CHIM PAY-B, V88, P732
  • [5] STUDIES OF CHROMENES .9. SYNTHESES OF CHROMENEQUINONES
    BROWN, PE
    LEWIS, RA
    WARING, MA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 2979 - 2988
  • [6] SYNTHESIS AND CYCLIZATION REACTIONS OF 4-[BIS(2-HYDROXYETHYL)AMINO]-9-(3-DIMETHYLAMINOPROPYLAMINO)-1-NITROACRIDINES - APPROACHES TO THE SYNTHESIS OF NITRACRINE MUSTARD
    CHAMBERS, D
    DENNY, WA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06): : 1055 - 1060
  • [7] DENNY WA, 1986, J MED CHEM, V14, P879
  • [8] NITROSOIMIDAZOLES - HIGHLY BACTERICIDAL ANALOGS OF 5-NITROIMIDAZOLE DRUGS
    EHLHARDT, WJ
    BEAULIEU, BB
    GOLDMAN, P
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (02) : 323 - 329
  • [9] Ellis G.P., 1977, CHROMENES CHROMANONE
  • [10] SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF SUBSTITUTED TRANS-4-AMINO-3,4-DIHYDRO-2,2-DIMETHYL-2H-1-BENZOPYRAN-3-OLS
    EVANS, JM
    FAKE, CS
    HAMILTON, TC
    POYSER, RH
    WATTS, EA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (11) : 1582 - 1589