Mild Synthesis of Symmetric 3,5-Disubstituted Nitrobenzenes

被引：0

作者：

Francisco, Telmo N. ^{[1
]}

Sousa, Joana L. C. ^{[1
]}

Guieu, Samuel ^{[1
,2
]}

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

Albuquerque, Helio M. T. ^{[1
]}

机构：

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

[2] Univ Aveiro, CICECO Aveiro Inst Mat, Dept Chem, P-3810193 Aveiro, Portugal

来源：

SYNLETT | 2022年 / 33卷 / 15期

关键词：

nitrobenzenes; formylchromones; nitromethane; Michael addition; Nef reaction; cascade reaction; OXIDATION;

D O I：

10.1055/a-1875-2646

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild synthesis of 3,5-disubstituted nitrobenzenes from readily available 3-formylchromones is reported. The developed methodology follows a cascade process, promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene. The proposed mechanism involves an initial Michael addition of nitromethane at C-2 of a 3-formylchromone. The resultant intermediate undergoes another Michael reaction with a second 3-formylchromone molecule. After ring closure through intramolecular cyclization, the aromatization is completed by deformylation, affording the 3,5-disubstituted nitrobenzenes in 52-86% yield. The reported method produces three new C-C bonds in a simple and straightforward manner, and it is consistent with gram-scale synthesis.

引用

页码：1505 / 1510

页数：6

共 25 条

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