Departamento de Química, Universidade Estadual de Maringá (UEM) , 87030-900 Maringá, PR, Brazil.
Departamento de Química, Universidade Federal de Santa Maria (UFSM) , 97110-970 Santa Maria, RS, Brazil.
J Org Chem. 2017 Dec 1;82(23):12590-12602. doi: 10.1021/acs.joc.7b02361. Epub 2017 Nov 15.
An alternative highly regioselective synthetic method for the preparation of 3,5-disubstituted 4-formyl-N-arylpyrazoles in a one-pot procedure is reported. The methodology developed was based on the regiochemical control of the cyclocondensation reaction of β-enamino diketones with arylhydrazines. Structural modifications in the β-enamino diketone system allied to the Lewis acid carbonyl activator BF were strategically employed for this control. Also a one-pot method for the preparation of 3,5-disubstituted 4-hydroxymethyl-N-arylpyrazole derivatives from the β-enamino diketone and arylhydrazine substrates is described.
报道了一种在一锅法中制备 3,5-二取代 4-甲酰基-N-芳基吡唑的高区域选择性的替代合成方法。所开发的方法基于β-烯胺二酮与芳基腙的环缩合反应的区域化学控制。β-烯胺二酮体系的结构修饰与路易斯酸羰基激活剂 BF 一起被策略性地用于这种控制。还描述了一种从β-烯胺二酮和芳基腙底物一锅法制备 3,5-二取代 4-羟甲基-N-芳基吡唑衍生物的方法。
