Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; unexpected reductions and vinylogations
作者:Attimogae Shivamurthy Harisha、Suresh Parameshwar Nayak、Kuppuswamy Nagarajan、Tayur Narasingarow Guru Row、Amar A. Hosamani
DOI:10.1016/j.tet.2016.03.097
日期:2016.6
Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined
在热乙醇中将2-氰基-3-(2-甲氧基-5-硝基苯基)丙烯酸乙酯1f暴露于三乙胺导致高产率地形成二氢衍生物2f和乙烯基化合物3f。提供了用于3f的单晶X射线数据。对于各种类似物观察到相似的反应。研究了改变芳基取代基,胺和溶剂的反应。还检查了吡啶基,噻吩基类似物。该研究扩展到包含这种系统,如噻唑烷二酮的环状分子8,3-氰基香豆素9和4-亚芳基-异喹啉-2,4-二酮11。最后一组给出了乙烯基化产物,4-肉桂基-异喹啉二酮和4-羟基化的物质。研究了来自丙二腈,乙酰乙酸乙酯,乙酰丙酮和甲基磺酰乙酸乙酯的亚芳基衍生物的一些实例。肉桂酸乙酯和β-硝基苯乙烯不受影响。由于添加自由基淬灭剂抑制了反应,因此认为该反应可能是自由基介导的。与热条件的影响相反,在254和365 nm的乙醇中1f的辐照产生复杂的混合物。在这项研究中还注意到了一些其他有趣的观察结果:1f与乙醛的乙烯基化反应生成3f;从1f形成3f用