A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-07-01 DOI:10.1039/D4OB00966E
Shaheen Fatma, Feroz Ahmad, Yogesh A. Pankhade, Pavit K. Ranga and Ramasamy Vijaya Anand
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Abstract

Herein, we report a transition-metal and base-free protocol to access a wide range of functionalized indenone derivatives through a HMPA–H2O-mediated oxygenative annulation of 2-alkynylphenyl-substituted p-quinone methides. This method worked effectively for most of the p-QMs investigated and the corresponding indenone derivatives were obtained in moderate to good yields. This methodology was further extended to the formal synthesis of one of the resveratrol based natural products, (±)-isopaucifloral F.

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在 HMPA-H2O 介导下,2-炔基苯基取代的对醌甲酰胺与茚酮发生氧代碳环化反应。
在此,我们报告了一种无过渡金属和碱的方案,通过 HMPA-H2O 介导的 2-炔基苯基取代对醌甲酰胺的氧环化反应,获得多种官能化的茚酮衍生物。这种方法对所研究的大多数对醌甲酰胺都有效,并能以中等至良好的产率获得相应的茚酮衍生物。该方法进一步扩展到白藜芦醇类天然产物之一 (±)-isopaucifloral F 的正式合成。
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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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