Sridharan Vellaisamy, Perumal Paramasivan T, Avendaño Carmen, Menéndez J Carlos
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040, Madrid, Spain.
Org Biomol Chem. 2007 May 7;5(9):1351-3. doi: 10.1039/b703083e. Epub 2007 Apr 4.
The reaction between aromatic imines and methacrolein dimethylhydrazone in the presence of 10% indium trichloride affords in good to excellent yields biologically and synthetically relevant 1,2,3,4-tetrahydroquinolines bearing a hydrazone function at C-4 in a one-pot process that involves the formation of two C-C bonds and the stereoselective generation of two stereocenters, one of them quaternary, and this constitutes the first example of an alpha,beta-unsaturated dimethylhydrazone behaving as a dienophile in a hetero Diels-Alder reaction and the first vinylogous aza-Povarov reaction.
在10%三氯化铟存在下，芳香亚胺与甲基丙烯醛二甲基腙反应，以良好至优异的产率，通过一锅法得到具有生物学和合成相关性的1,2,3,4-四氢喹啉，该方法涉及形成两个C-C键以及两个立体中心的立体选择性生成，其中一个是季碳中心，这构成了α,β-不饱和二甲基腙在杂环Diels-Alder反应中作为亲双烯体的首个实例，也是首个乙烯型氮杂-Povarov反应。
