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.

引用

页码：708 / 712

页数：5

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