A three-component reaction between trialkyl phosphites or triphenylphosphine, dimethyl acetylenedicarboxylate and N-aryl-3-hydroxynaphthalene-2-carboxamide

被引：27
|
作者：
Anary-Abbasinejad, Mohammad [1 ]
Hassanabadi, Alireza [1 ]
Mazraeh-Seffid, Manouchehr [1 ]
机构：
[1] Islamic Azad Univ, Dept Chem, Yazd Branch, Yazd, Iran
来源：
JOURNAL OF CHEMICAL RESEARCH | 2007年 / 12期
关键词：
dimethyl acetylenedicarboxylate; thialkyl phosphites; N-aryl-3-hydroxynaphthalene-2-carboxamide; stereoselective synthesis; triphenylphosphine;
D O I：
10.3184/030823407X272138
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A three-component reaction between dimethyl acetylenedicarboxylate (DMAD) and trialkyl phosphites in the presence of N-aryl-3-hydroxynaphthalene-2-carboxamide leads to dialkyl 2-(dimethoxyphosphoryl)-3-[2-hydroxy3-(arylcarbamyl)naphthalen-1-yl] succinate in excellent yields. A similar reaction with triphenylphosphine, instead of phosphites, produces dimethyl 2-[2-hydroxy-3-(arylcarbamoyl)naphthalen-1-yl]lmaleates. In the absence of triphenylphosphine or phosphite, DMAD adds to N-aryl-3-hydroxynaphthalene-2-carboxamide to produce alkyl 2-(alkoxycarbonylmethyl)-4-oxo-3-aryl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-2-carboxylates in good yields.
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页码：708 / 712
页数：5
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