期刊
GREEN CHEMISTRY
卷 21, 期 23, 页码 6381-6389出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9gc02824b
关键词
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资金
- Russian Science Foundation (RSF) [18-74-00094]
- Program of fundamental research for state academies for 2013-2020 [01201363818]
- Russian Science Foundation [18-74-00094] Funding Source: Russian Science Foundation
Azodicarboxylate esters are common reagents in organic synthesis laboratories due to their utility in the Mitsunobu reaction. They can also be regarded as possible starting compounds for C-H functionalization, which up until now has been mainly achieved by transition-metal-catalyzed reactions. We have developed a novel reaction involving the quantitative coupling of 8-hydroxyquinoline or phenol with azodicarboxylate esters. The functionalization proceeds under mild base-catalyzed conditions selectively, and either the ortho-position of 8-hydroxyquinoline or para-position of the phenol/naphthol is involved in the reaction. This type of transformation can be considered as hydrazo coupling (by analogy with azo coupling). Herein, we discuss a plausible mechanism for this catalyzed substitution, backing up our findings with deuterium NMR experiments and by varying the starting compounds and bases. Using Boc-NN-Boc as a substrate, we have developed the convenient and efficient synthesis of (8-hydroxyquinolin-7-yl)hydrazines, as well as demonstrating a new stereoselective route for the synthesis of medicinally important 4-hydroxyphenylhydrazine for laboratory use, which almost doubles the yield of the common industrial process and reduces the number of synthetic steps. A new one-pot procedure for the synthesis of aromatic 8-hydroxyquinolin-7-yl hydrazones was applied.
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