Peng Cheng, Zhang Jingyi, Xue Jian, Li Siqi, Wang Xiao-Na, Chang Junbiao
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou 450001 , P. R. China.
J Org Chem. 2018 Aug 17;83(16):9256-9266. doi: 10.1021/acs.joc.8b01255. Epub 2018 Jul 13.
Two complementary synthetic manifestations leading to highly substituted 1-naphthol and 2-naphthol derivatives via Lewis acids catalyzed annulations of ynamides with acyl chlorides are described here. A one-pot synthesis of 4-amino-2-naphthol derivatives is accomplished via a ZnI-catalyzed tandem Friedel-Crafts reaction sequence. While in the presence of Pd(0) catalyst, a [2 + 2] cycloaddition reaction of ynamides with monosubstituted ketenes that were generated from the dehydrohalogenation of suitable acyl chlorides leads to efficient formation of 3-aminocyclobutenones, which were subsequently modified to generate 3-amino-1-naphthols in excellent yields.
本文描述了两种互补的合成方法，通过路易斯酸催化的炔酰胺与酰氯的环化反应生成高度取代的1-萘酚和2-萘酚衍生物。通过ZnI催化的串联傅克反应序列实现了4-氨基-2-萘酚衍生物的一锅法合成。而在Pd(0)催化剂存在下，炔酰胺与由合适酰氯脱卤化氢生成的单取代烯酮发生[2 + 2]环加成反应，可高效生成3-氨基环丁烯酮，随后对其进行修饰，以优异的产率生成3-氨基-1-萘酚。
