Novel dicyanomethylene compounds from the reaction of 2-aryl-2,3-dihydro-1H-pyrrolo[3,4-b] quinoxalines with ethenetetracarbonitrile

被引：4
作者：
Hassan, Alaa A. [1 ]
El-Shaieb, Kamal M.
Doepp, Dietrich
机构：
[1] Menia Univ, Fac Sci, Dept Chem, El Minia, Egypt
[2] Univ Duisburg Gesamthsch, D-47048 Duisburg, Germany
来源：
ARKIVOC | 2005年
关键词：
azaisoindoles; dehydrogenation; nitrenes; oxygenation;
D O I：
10.3998/ark.5550190.0006.a12
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Aryl-2,3-dihydro-1H-pyrrolo[3,4-b] quinoxalines 8a-d react with ethenetetracarbonitrile (TCNE) in aerated benzene with formation of [3-(2-aryl-3-dicyanomethylene-2,3-dihydro-1H-pyrrolo[ 3,4-b] quinoxalin-1-ylidene)-2-aryl-2,3-dihydro-1H-pyrrolo[3,4-b] quinoxalin-1-ylidene] propanedinitriles 9a-d (41 - 48%), [2-aryl-3-arylimino-2,3-dihydro-1H-pyrrolo[3,4-b]quinoxalin-1-ylidene] propanedinitriles 10a-d (19 - 22%) as well as quinoxaline-2,3-diol (11, 8 - 11%). Rationales for these transformations are presented.
引用
收藏
页码：139 / 149
页数：11
相关论文
共 29 条
  • [1] ANDERSON RC, 1969, TETRAHEDRON LETT, P1581
  • [2] SYNTHESIS AND STABILITY OF 2-METHYL-2,4-DIAZA-INDENE AND 2-METHYL-2,5-DIAZA-INDENE + (2-METHYL-PYRROLO[3,4-B]PYRIDINE AND PYRROLO[3,4-C]PYRIDINE)
    ARMAREGO, WL
    MILLOY, BA
    SHARMA, SC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (20): : 2485 - &
  • [3] HYDROGEN-CYANIDE CHEMISTRY .4. DIIMINOSUCCINONITRILE REACTIONS WITH NUCLEOPHILES, ACYL HALIDES, AND CARBONYL-COMPOUNDS
    BEGLAND, RW
    HARTTER, DR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (25) : 4136 - 4145
  • [4] SUBSTITUTION AND ADDITION-REACTIONS OF ISOINDOLES
    BONNETT, R
    NORTH, SA
    NEWTON, RF
    SCOPES, DIC
    [J]. TETRAHEDRON, 1983, 39 (08) : 1401 - 1405
  • [5] Bonnett R., 1981, ADV HETEROCYCL CHEM, V29, P341
  • [6] Bruni P, 1997, GAZZ CHIM ITAL, V127, P435
  • [7] 7-AZABENZONORBORNADIENE
    CARPINO, LA
    BARR, DE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (03) : 764 - &
  • [8] 1,1,2-TRIPHENYLBENZOCYCLOBUTENE
    CARPINO, LA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (02) : 461 - &
  • [9] SYNTHESIS, CHARACTERIZATION, AND THERMOLYSIS OF 7-AMINO-7-AZABENZONORBORNADIENES
    CARPINO, LA
    PADYKULA, RE
    BARR, DE
    HALL, FH
    KRAUSE, JG
    DUFRESNE, RF
    THOMAN, CJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) : 2565 - 2572
  • [10] New reaction of ethenetetracarbonitrile with N-arylisoindolines
    Döpp, D
    Hassan, AA
    Mourad, AFE
    El-Din, AMN
    Angermund, K
    Krüger, C
    Lehmann, CW
    Rust, J
    [J]. TETRAHEDRON, 2003, 59 (27) : 5073 - 5081
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