Synthesis of spirodienones by intramolecular ipso-cyclization of N-methoxy-(4-halogenophenyl)amides using [hydroxy(tosyloxy)iodo]benzene in trifluoroethanol

被引:59
作者
Miyazawa, E [1 ]
Sakamoto, T [1 ]
Kikugawa, Y [1 ]
机构
[1] Josai Univ, Fac Pharmaceut Sci, Sakado, Saitama 3500295, Japan
关键词
D O I
10.1021/jo034318w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Spirodienones bearing the 1-azaspiro[4.5]decane ring system have been synthesized from N-methoxy-(4-halogenophenyl)amides by the intramolecular ipso attack of a nitrenium ion generated with [hydroxy(tosyloxy)iodo]-benzene in trifluoroethanol.
引用
收藏
页码:5429 / 5432
页数:4
相关论文
共 17 条
  • [1] LEPADIFORMINE, A NEW MARINE CYTOTOXIC ALKALOID FROM CLAVELINA-LEPADIFORMIS MULLER
    BIARD, JF
    GUYOT, S
    ROUSSAKIS, C
    VERBIST, JF
    VERCAUTEREN, J
    WEBER, JF
    BOUKEF, K
    [J]. TETRAHEDRON LETTERS, 1994, 35 (17) : 2691 - 2694
  • [2] CYLINDRICINE-A AND CYLINDRICINE-B, NOVEL ALKALOIDS FROM THE ASCIDIAN CLAVELINA-CYLINDRICA
    BLACKMAN, AJ
    LI, CP
    HOCKLESS, DCR
    SKELTON, BW
    WHITE, AH
    [J]. TETRAHEDRON, 1993, 49 (38) : 8645 - 8656
  • [3] THE FORMATION AND REDUCTIVE SCISSION OF BIS-COMPOUNDS FROM ENOLS
    BRADLEY, W
    WATKINSON, LJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1956, (FEB): : 319 - 327
  • [4] Efficient oxidative spirocyclization of phenolic sulfonamides
    Canesi, S
    Belmont, P
    Bouchu, D
    Rousset, L
    Ciufolini, MA
    [J]. TETRAHEDRON LETTERS, 2002, 43 (29) : 5193 - 5195
  • [5] ALKOXYNITRENIUM ION CYCLIZATIONS - EVIDENCE FOR DIFFERENT MECHANISMS IN THE FORMATION OF BENZOXAZINES AND BENZOXAZEPINES
    GLOVER, SA
    ROWBOTTOM, CA
    SCOTT, AP
    SCHOONRAAD, JL
    [J]. TETRAHEDRON, 1990, 46 (20) : 7247 - 7262
  • [6] N-ALKOXY-N-ACYLNITRENIUM IONS IN INTRAMOLECULAR AROMATIC ADDITION-REACTIONS
    GLOVER, SA
    GOOSEN, A
    MCCLELAND, CW
    SCHOONRAAD, JL
    [J]. TETRAHEDRON, 1987, 43 (11) : 2577 - 2592
  • [7] ELECTROPHILIC AROMATIC-SUBSTITUTION WITH N-METHOXY-N-ACYLNITRENIUM IONS GENERATED FROM N-CHLORO-N-METHOXYAMIDES - SYNTHESES OF NITROGEN HETEROCYCLIC-COMPOUNDS BEARING A N-METHOXYAMIDE GROUP
    KAWASE, M
    KITAMURA, T
    KIKUGAWA, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) : 3394 - 3403
  • [8] THE PREFERENTIAL MIGRATION TENDENCY OF THE ALKOXYAMIDE GROUP IN THE DIENONE PHENOL REARRANGEMENT
    KIKUGAWA, Y
    KITAMURA, T
    KAWASE, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (09) : 525 - 527
  • [9] Miyazawa E, 2003, HETEROCYCLES, V59, P149
  • [10] AlCl3-mediated migration of the benzamido group of N-phenoxybenzamide derivatives to the phenyl group
    Miyazawa, E
    Sakamoto, T
    Kikugawa, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (01): : 7 - 11