通过[2 + 2]环加成将N-甲苯磺酰基乙亚氨酸酯/乙亚胺酰胺引入芳炔
Insertion of N-Tosylacetimidates/Acetimidamides onto Arynes via [2 + 2] Cycloaddition.
作者信息
Kranthikumar Ramagonolla, Chegondi Rambabu, Chandrasekhar Srivari
机构信息
CSIR-Indian Institute of Chemical Technology , Division of Natural Product Chemistry, Hyderabad 500007, India.
出版信息
J Org Chem. 2016 Mar 18;81(6):2451-9. doi: 10.1021/acs.joc.5b02907. Epub 2016 Mar 10.
A novel insertion reaction of N-tosylacetimidates and N-tosylacetimidamides onto arynes via a benzocyclobutene intermediate followed by ring cleavage is developed to afford o-benzylbenzoic acid derivatives in good yields. Interestingly, the use of cyclic 2-sulfonyliminoindolines provided two distinct products such as azepanimines via [2 + 2] cycloaddition and indolamines via protonation based on solvent medium.
通过苯并环丁烯中间体，随后进行环裂解，开发了一种新颖的N-甲苯磺酰基乙亚氨酸酯和N-甲苯磺酰基乙亚氨酰胺与芳炔的插入反应，以高产率得到邻苄基苯甲酸衍生物。有趣的是，基于溶剂介质，使用环状2-磺酰基亚氨基吲哚啉会提供两种不同的产物，例如通过[2 + 2]环加成得到氮杂环庚三烯胺，以及通过质子化得到吲哚胺。
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