1,6-Conjugated Addition of Nitromethane to (E)-2-Styrylchromones: A New Synthesis of Novel 2-Substituted 4-Arylpyrrole Derivatives

被引：8

作者：

Silva, Eduarda M. P. ^{[1
]}

Silva, Artur M. S. ^{[1
]}

Cavaleiro, Jose A. S. ^{[1
]}

机构：

[1] Univ Aveiro, Dept Chem, QOPNA, P-3810193 Aveiro, Portugal

来源：

SYNLETT | 2011年 / 18期

关键词：

(E)-2-styrylchromones; nitromethane; 1,6-conjugated addition; 1,4-Michael addition; 2-substituted; 4-arylpyrroles; DBU; POLYHYDROXYLATED; 2-STYRYLCHROMONES; BIOLOGICAL-ACTIVITIES; CONJUGATE ADDITION;

D O I：

10.1055/s-0031-1289525

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,6-conjugate addition of nitromethane to (E)-2-styrylchromones were achieved, in moderate to good yields, by using DBU as organocatalyst. Reduction studies on the 2-(2-aryl-3-nitropropyl) chromone adducts formed surprisingly led to novel 2-substituted 4-arylpyrrole derivatives. These new derivatives are formed from nitro-group reduction, followed by a 1,4-Michael-type addition of the primary amine intermediate to the alpha, beta-unsaturated carbonyl system of the chromone moiety and concomitant heterocyclic ring opening.

引用

页码：2740 / 2744

页数：5

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