LiOBu促进的2'-炔基-联芳基-2-醛-对甲苯磺酰腙的分子内1,3-偶极环加成反应：合成3-取代的1-二苯并[,]吲唑的方法
LiOBu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2'-Alkynyl-biaryl-2-aldehyde -Tosylhydrazones Approach to 3-Substituted 1-Dibenzo[,]indazoles.
作者信息
Lv Jiaying, Hua Ruimao
机构信息
Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China.
State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, China.
出版信息
Molecules. 2023 Dec 13;28(24):8061. doi: 10.3390/molecules28248061.
A two-step, one-pot synthesis of 3-substituted 1-dibenzo[,]indazoles in good to high yields via a LiOBu-promoted intramolecular 1,3-dipolar cyclization of 2'-alkynyl-biaryl-2-aldehyde -tosylhydrazones was developed. The -Ts-hydrazones used were prepared in situ via the reactions of 2'-alkynyl-biaryl-2-aldehydes and TsNHNH-methylbenzenesulfonohydrazide). Two types of signals related to the hydrogen bonds, forming in several products, were observed in the H NMR spectra recorded in DMSO-, assigned to N-H bonds in their dimeric species of product and tautomer.
通过LiOBu促进的2'-炔基-联芳基-2-醛对甲苯磺酰腙的分子内1,3-偶极环化反应，开发了一种两步一锅法合成3-取代的1-二苯并[，]吲唑的方法，产率良好至高。所用的对甲苯磺酰腙通过2'-炔基-联芳基-2-醛与对甲苯磺酰肼（对甲苯磺酰甲基苯磺酰肼）的反应原位制备。在DMSO-中记录的1H NMR光谱中观察到与几种产物中形成的氢键相关的两种信号，它们归因于产物二聚体及其互变异构体中的N-H键。
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