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Synthesis of 2,3-Dialkyl-5-hydroxybenzofurans via a One-pot, Three-step Reaction Sequence of 2-Monosubstituted 1,3-Diketones and 1,4-Benzoquinones
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2024-05-02 , DOI: 10.1021/acs.joc.4c00511
Qing Dong 1 , Yu-Huan Yang 1 , Xue-Jiao Lv 1 , Jia-Hui Liu 1 , Yan-Kai Liu 1, 2
Affiliation  

An economical one-pot, three-step reaction sequence of readily available 2-monosubstituted 1,3-diketones and 1,4-benzoquinones has been explored for the facile access of 2,3-dialkyl-5-hydroxybenzofurans. By using cheap K2CO3 and conc. HCl as the reaction promoters, the reaction occurs smoothly via sequential Michael addition, aromatization, retro-Claisen, deacylation, hemiketalization, and dehydration processes under mild conditions in a practical manner. Additionally, an interesting phenomenon was observed during the derivatization studies, where the dihydroquinoline was converted into tetrahydroquinoline and quinoline products, respectively, via a disproportionation process.

中文翻译:

通过2-单取代1,3-二酮和1,4-苯醌的一锅三步反应序列合成2,3-二烷基-5-羟基苯并呋喃

为了方便地获得 2,3-二烷基-5-羟基苯并呋喃,我们探索了一种经济的一锅三步反应序列,由容易获得的 2-单取代 1,3-二酮和 1,4-苯醌组成。通过使用廉价的 K 2 CO 3和浓缩物。以HCl为反应促进剂,通过连续的迈克尔加成、芳构化、逆克莱森、脱酰化、半缩酮化和脱水等过程,反应在温和条件下顺利进行,实用性强。此外,在衍生化研究过程中观察到一个有趣的现象,即二氢喹啉通过歧化过程分别转化为四氢喹啉和喹啉产物。
更新日期:2024-05-02
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