Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition

被引：26

作者：

Raimondi, Wilfried ^{[1
]}

Dauzonne, Daniel ^{[2
,3
]}

Constantieux, Thierry ^{[1
]}

Bonne, Damien ^{[1
]}

Rodriguez, Jean ^{[1
]}

机构：

[1] Aix Marseille Univ, CNRS, iSm2, UMR 7313, F-13397 Marseille, France

[2] Inst Curie, Ctr Rech, F-75005 Paris, France

[3] CNRS, UMR 176, F-75005 Paris, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 31期

关键词：

Oxygen heterocycles; Phosphorus; Cycloaddition; Domino reactions; Regioselectivity; ONE-POT SYNTHESIS; POLYSUBSTITUTED FURANS; BIOLOGICAL EVALUATION; MICHAEL ADDITION; CATALYZED CYCLOISOMERIZATION; 1,2-DICARBONYL COMPOUNDS; TETRASUBSTITUTED FURANS; GENERAL-SYNTHESIS; EFFICIENT; ALKYNES;

D O I：

10.1002/ejoc.201201192

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Functionalized furans are very easily synthesized by exploiting the dual nucleophilic character of 1,2-dicarbonyls and the dual electrophilic properties of (2-chloro-2-nitroethenyl)benzenes in a one-pot, formal [3+2] cycloaddition. Using a base (DBU), the desired trisubstituted heterocycles were formed rapidly (1030 min) in good to excellent yields (5192?%), and this versatile, metal-free methodology was applied to the synthesis of 2-acyl- and 2-carboalkoxyfurans and furan-2-carboxamides. Additionally, by using 2-ketophosphonate derivatives as dinucleophiles, the corresponding 2-phosphorylfurans were formed in good yields (5374?%).

引用

页码：6119 / 6123

页数：5

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