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
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