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Nitromethane as a surrogate cyanating agent: 7-N,N-dimethylamino-4-hydroxycoumarin-catalyzed, metal-free synthesis of α-iminonitriles
Green Chemistry ( IF 9.8 ) Pub Date : 2020-11-03 , DOI: 10.1039/d0gc03411h
Iddum Satyanarayana, Kiran B. Manjappa, Ding-Yah Yang

An efficient, metal/alkali-cyanide free approach for the synthesis of α-iminonitriles via kinetically controlled, base-mediated and 1,3-diketone-catalyzed reaction is reported. The preparation of target compounds was realized by condensation of substituted anilines and aldehydes in nitromethane as a surrogate cyanating agent and as a solvent. This strategy was further improved by replacing aldehydes and nitromethane with β-nitrostyrene and ethanol, respectively, rendering the methodology greener. The catalytic role played by 1,3-diketones such as 7-N,N-dimethylamino-4-hydroxycoumarin in this three-component reaction was investigated, and a plausible mechanism was proposed based on control experiments.

中文翻译:

硝基甲烷作为替代氰化剂:7-N,N-二甲基氨基-4-羟基香豆素催化的无金属合成α-亚氨基腈

报道了一种通过动力学控制的,碱介导的和1,3-二酮催化的反应合成α-亚胺的有效的无金属/碱金属氰化物的方法。通过将取代的苯胺和醛在硝基甲烷中作为替代氰化剂和溶剂缩合,可以实现目标化合物的制备。通过分别用β-硝基苯乙烯和乙醇代替醛和硝基甲烷,进一步改善了该策略,从而使该方法更加环保。研究了7,NN-二甲基氨基-4-羟基香豆素等1,3-二酮在该三组分反应中的催化作用,并在控制实验的基础上提出了可能的机理。
更新日期:2020-11-09
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