氨基甲酸酯和酰胺亚硝基Diels-Alder环加成物与1,2-二氢吡啶的杂Cope重排反应可得到新颖的四氢吡啶烯酰胺和烯氨基甲酸酯,详细研究了最佳反应条件。当处理氨基甲酸酯亚硝基环加合物时,获得在C-4位上含有游离OH的四氢吡啶酰胺和氨基甲酸酯的可能性仅限于特定的取代方式。另一方面,从容易获得的酰胺亚硝基环加合物和催化量的亚铜盐开始,现在可以得到几种取代的4a,7,8a-四氢吡啶并[4,3- e ]-[1,4,2]二恶嗪产量中等至良好。
Synthesis of Protected (1-Phenyl-1<i>H</i>-pyrrol-2-yl)-alkane-1-amines from Phenylnitroso Diels–Alder Adducts with 1,2-Dihydropyridines
作者:Francesco Berti、Valeria Di Bussolo、Mauro Pineschi
DOI:10.1021/jo4009996
日期:2013.7.19
The reductive cleavage of nitrosobenzene-derived cycloadducts with appropriately protected 1,2-dihydropyridines allows a novel and simple obtainment of substituted N-[1-(1-phenyl-1H-pyrrol-2-yl)alkylamides. This synthesis can also be carried out in a very simple, mild, and practical one-pot procedure without isolation of the corresponding nitrosobenzene cycloadduct by means of catalytic amounts of