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Lewis Acids Catalyzed Annulations of Ynamides with Acyl Chlorides for Constructing 4-Amino-2-naphthol Derivatives and 3-Aminocyclobutenones
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-07-06 00:00:00 , DOI: 10.1021/acs.joc.8b01255
Cheng Peng 1 , Jingyi Zhang 1 , Jian Xue 1 , Siqi Li 1 , Xiao-Na Wang 1 , Junbiao Chang 1
Affiliation  

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 ZnI2-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.

中文翻译:

Lewis Acids用酰氯催化的酰胺环用于构建4-氨基-2-萘酚衍生物和3-氨基环丁烯酮

本文描述了两种互补的合成表现形式,它们通过路易斯酸催化的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。一锅合成4-氨基-2-萘酚衍生物是通过ZnI 2催化的串联Friedel-Crafts反应序列完成的。在Pd(0)催化剂存在的情况下,酰胺由适当的酰氯脱卤化氢生成的单取代烯酮与[2 + 2]环加成反应,可有效形成3-氨基环丁烯酮,随后对其进行修饰以生成3 -氨基-1-萘酚具有优异的收率。
更新日期:2018-07-06
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