Ring contraction in reactions of 3-benzoylquinoxalin-2-ones with 1,2-phenylenediamines. Quinoxaline-benzoimidazole rearrangement

被引:0
|
作者
V. A. Mamedov
A. A. Kalinin
A. T. Gubaidullin
A. V. Chernova
I. A. Litvinov
Ya. A. Levin
R. R. Shagidullin
机构
[1] Kazan Research Center of the Russian Academy of Sciences,A. E. Arbuzov Institute of Organic and Physical Chemistry
来源
Russian Chemical Bulletin | 2004年 / 53卷
关键词
3-benzoylquinoxalin-2-ones; 1,2-phenylenediamines; benzoimidazole; pyrazine-imidazole ring contraction; rearrangements; IR spectra; H NMR spectra; X-ray diffraction analysis;
D O I
暂无
中图分类号
学科分类号
摘要
The reactions of 3-benzoylquinoxalin-2-one and its N(1)-alkyl derivatives with 1,2-phenylenediamines were accompanied by ring contraction as a result of the quinoxaline-benzoimidazole rearrangement giving rise to 2-benzoimidazolyl-substituted quinoxalines. The possible pathways of these reaction are discussed.
引用
收藏
页码:164 / 175
页数:11
相关论文
共 50 条
  • [41] ORGANIC SELENIUM-COMPOUNDS .2. REACTIONS OF 2-SUBSTITUTED 1,2-BENZOISOSELENAZOL-3(2H)-ONES
    DALLACKER, F
    PEISKER, A
    CHEMIKER-ZEITUNG, 1991, 115 (06): : 169 - 172
  • [42] NEW RING TRANSFORMATION OF 3-HALO-2-AZIDOPYRIDINE 1-OXIDES - NOVEL SYNTHESIS OF 1,2-OXAZIN-6-ONES
    ABRAMOVITCH, RA
    SHINKAI, I
    CUE, BW
    RAGAN, FA
    ATWOOD, JL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (02) : 415 - 417
  • [43] REACTIONS OF PYRANO[3,4-B]INDOL-3-ONES WITH DIENOPHILES - CONSECUTIVE [4 + 2] CYCLOADDITION CYCLOREVERSION/1,2 ELIMINATION
    PINDUR, U
    ERFANIANABDOUST, H
    LIEBIGS ANNALEN DER CHEMIE, 1989, (12): : 1275 - 1276
  • [44] Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes
    Attanas, Orazio A.
    Favi, Gianfranco
    Giorgi, Gianluca
    Mantellini, Fabio
    Karapetyan, Vahuni
    Langer, Peter
    TETRAHEDRON, 2009, 65 (28) : 5456 - 5461
  • [45] SYNTHESIS AND REARRANGEMENT REACTIONS OF 3-(1,2,3,4-TETRA-HYDRO-1-ISOQUINOLINE-METHYLENE)-DELTA-2-1,2,4-OXADIAZOLIN-5-ONES
    TAKACS, K
    HETEROCYCLES, 1984, 21 : 703 - 703
  • [46] 1,3,2-THIAZAPHOSPHOLIDIN-2-ONES DERIVED FROM EPHEDRINE - PREPARATION AND STEREOCHEMISTRY OF RING-OPENING REACTIONS
    HALL, CR
    WILLIAMS, NE
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (10): : 2746 - 2750
  • [47] Synthesis and ring transformations of 1-amino-1,2,3,9a-tetrahydroimidazo[ 1,2-a]indol-2(9H)-ones
    Dumciute, J
    Martynaitis, V
    Holzer, W
    Mangelinckx, S
    De Kimpe, N
    Sackus, A
    TETRAHEDRON, 2006, 62 (14) : 3309 - 3319
  • [48] A facile acid catalysed ring transformation of 4H-pyrans to 1,2,3,4-tetrahydropyridin-2-ones and 3,4-dihydronaphtho[1,2-b]pyran-2(H)-ones
    Srivastava, S
    Batra, S
    Bhaduri, AP
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (06): : 602 - 604
  • [49] Synthesis of dispiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizine-2′,2"-[1,3]thiazolo[3,2-a]pyrimidine via cycloaddition reactions
    Ren, Demin
    Hu, Xiaolian
    Huang, Yulin
    Li, Xiaofang
    JOURNAL OF CHEMICAL RESEARCH, 2018, (09) : 453 - 455
  • [50] 4-IMINO-4,5-DIHYDRO-1,2-LAMBDA-6-3-OXATHIAZOL-2-ONES - RING-OPENING CYCLO-ADDITION REACTIONS WITH MAINTENANCE OF THE RING SIZE
    LABBE, G
    YU, CC
    TOPPET, S
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22): : 3991 - 3994