ISOMERIZATION OF DIETHYL 1-ALKYNYLPHOSPHONATES TO 1,3-DIENYLPHOSPHONATES FOLLOWED BY DIELS-ALDER REACTION WITH DEAD, MALEIC ANHYDRIDE AND MALEIMIDE

被引：10

作者：

Azab, Abdullatif ^{[1
]}

Quntar, Abed Al Aziz ^{[1
,2
]}

Antebi, Tamar ^{[1
]}

Srebnik, Morris ^{[1
]}

机构：

[1] Hebrew Univ Jerusalem, Inst Drug Res, Sch Pharm, IL-91120 Jerusalem, Israel

[2] Al Quds Univ, Dept Mat Engn, Fac Engn, Jerusalem, Israel

来源：

HETEROCYCLES | 2010年 / 82卷 / 01期

基金：

以色列科学基金会;

关键词：

Palladium(0); Diene; Stereoselective Reaction; Endo-Adduct; Half-Chair; VINYLPHOSPHONATES; CYCLOADDITION; 1,3-DIENES; ALKYNES; RHODIUM;

D O I：

10.3987/COM-10-S(E)12

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isomerization of diethyl 1-alkynylphosphonates, 1, with Pd[(PPh)(3)](4) in refluxing 1,4-dioxane provides 1,3-dienylphosphonates, 2, in satisfactory to excellent isolated yield (45-83%). The reaction is tolerant of chlorides and cyclic substituents. Cycloaddition reaction of 2 with DEAD provided the corresponding diethyl 3-(diethoxyphosphoryl)-6-alkyl-3,6-dihydropyridazine-1,2-dicarboxylates, 3, in 85% isolated yield. The cycloaddition products can be obtained in a one-pot reaction directly from the isomerized 1-alkynylphosphonates with no loss in yields. Similarly, 1,3-dioxo-1,3,3a,4,7,7a-hexahydroisobenzofuran-4-ylphosphonate, and 1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindo1-4-ylphosphonate 4 were obtained by reacting 1,3-dienylphosphonates with maleic anhydride and maleimide respectively.

引用

页码：417 / 429

页数：13

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