Reactions of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)oxoacetates.: Synthesis of methyl isoxazolo[5,4-a]carbazole-3-carboxylates

被引：0
|
作者：
Martin, Arputharaj Ebenezer [1 ]
Prasad, Karnam Jayarampillai Rajendra [1 ]
机构：
[1] Bharathiar Univ, Dept Chem, Coimbatore 641046, Tamil Nadu, India
来源：
JOURNAL OF CHEMICAL RESEARCH | 2007年 / 11期
关键词：
carbazoles; fused isoxazoles; alpha-ketoesters;
D O I：
10.3184/030823407X266324
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reaction of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)oxoacetates (1a-e) with hydroxylamine hydrochloride in alcoholic KOH afforded 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles (2a-e), and in acetic acid methyl isoxazolo[5,4-a]carbazole-3-carboxylates (3a-e). Ketoesters 1a-e with urea and thiourea under acidic conditions yielded a mixture of the respective 1-hydroxycarbazoles (6a-e) and 2,3,4,9-tetrahydro-1H-carbazol-1-ones (7a-e), but under basic conditions the respective 1-carbimido- and 1-thiocarbimido-2,3,4,9-tetrahydro-1H-carbazoles (8a-e and 9a-e) were formed. Plausible mechanisms are proposed.
引用
收藏
页码：653 / 656
页数：4
相关论文
共 50 条
  • [1] Methyl 1-oxo-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate
    Thiruvalluvar, A.
    Gunaseelan, A. Thomas
    Martin, A. Ebenezer
    Prasad, K. J. Rajendra
    Butcher, R. J.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3622 - U4580
  • [2] Ethyl 2-(9-methylsulfonyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetate
    Ozbey, Suheyla
    Karayel, Arzu
    Yilmaz, Ayhan
    Uludag, Nesimi
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O1623 - O1625
  • [3] Methyl 9-methyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate
    Thiruvalluvar, A.
    Gunaseelan, A. Thomas
    Martin, A. Ebenezer
    Prasad, K. J. Rajendra
    Butcher, R. J.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3093 - U2492
  • [4] 2-{N-[(2,3,4,9-Tetrahydro-1H-carbazol-3-yl)methyl]methylsulfonamido}ethyl methanesulfonate
    Gocmenturk, Mustafa
    Ergun, Yavuz
    Mougang-Soume, Berline
    Delibas, Nagihan Caylak
    Hokelek, Tuncer
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O78 - +
  • [5] 2-(6-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-ylidene)propanedinitrile
    Sekar, M.
    Velmurugan, R.
    Chandramohan, A.
    Ramesh, P.
    Ponnuswamy, M. N.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3270 - U459
  • [6] 2-{4-Methyl-N-[(2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl] benzenesulfon-amido}ethyl 4-methylbenzenesulfonate
    Gocmenturk, Mustafa
    Ergun, Yavuz
    Mougang-Soume, Berline
    Delibas, Nagihan Caylak
    Hokelek, Tuncer
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1797 - +
  • [7] Syntheses of methyl 4,5-dihydro-2H-pyrazolo[3,4-a]carbazole-3-carboxylates
    Martin, Arputhari Ebenezer
    Prasad, Karnam Jayarampillai Rajendra
    JOURNAL OF CHEMICAL RESEARCH-S, 2006, (07): : 473 - 477
  • [8] (E)-2-[(Furan-2-yl)methylidene]-7-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one
    Thiruvalluvar, A.
    Archana, R.
    Yamuna, E.
    Prasad, K. J. Rajendra
    Butcher, R. J.
    Gupta, Sushil K.
    Yildirim, Sema Ozturk
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O150 - +
  • [9] 2-(2,3,4,9-Tetrahydro-1H-carbazol-1-ylidene)propanedinitrile
    Archana, R.
    Prabakaran, K.
    Prasad, K. J. Rajendra
    Thiruvalluvar, A.
    Butcher, R. J.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1713 - U641
  • [10] 9-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one
    Thiruvalluvar, A.
    Gunaseelan, A. Thomas
    Martin, A. Ebenezer
    Prasad, K. J. Rajendra
    Butcher, R. J.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3524 - U3639
12345