{“_”：“炔基连接吲哚的区域选择性氧胺化环化制备官能化δ-卡波姆-氧化物。”，“i”：[“N”]}
{"_":"Regioselective Oxyamination Cyclization of Alkynyl-Tethered Indoles to Prepare Functionalized δ-Carboline -Oxides.","i":["N"]}
摘要(中文译文)
我们报道了一种无过渡金属参与的方法，通过亚硝酸叔丁酯（TBN）介导的炔基连接吲哚的分子内氧胺化环化反应，以良好收率和高区域选择性制备多种官能化δ-咔啉氧化物。机理研究表明，该级联反应涉及TBN介导的吲哚部分亚硝化生成肟，随后炔烃部分的区域选择性6-外环化，HO对亲电烯烃部分的亲核加成，以及醇在一锅反应中经四步氧化为酮。所获得的官能化δ-咔啉氧化物可容易地转化为官能化δ-咔啉，并且从雌酮出发经四步以总收率24%获得雌酮衍生的δ-咔啉氧化物。
Abstract
We report a transition-metal free approach to prepare a variety of functionalized δ-carboline -oxides in good yields with high regioselectivity through -butyl nitrite (TBN)-mediated intramolecular oxyamination cyclization of alkynyl-tethered indoles. Mechanistic studies show that the cascade reaction involves TBN-mediated nitrosation of indole moiety to oxime, followed by a regioselective 6--dig cyclization of alkyne moiety, nucleophilic addition of HO to the electrophilic alkene moiety, and oxidation of alcohol to ketone over four steps in a one-pot reaction. The obtained functionalized δ-carboline -oxides could be easily converted into functionalized δ-carbolines and an estrone derived δ-carboline -oxide is obtained in total 24% yield from estrone in four steps.
如何引用
AMA
Jin Zhao, Yuan-Yuan Fan, Zhong-Chen Huang, Jia-Qian Zhang, Pei-Wen Qiu, Wan-Yun Huang, et al. {"_":"Regioselective Oxyamination Cyclization of Alkynyl-Tethered Indoles to Prepare Functionalized δ-Carboline -Oxides.","i":["N"]}. The Journal of organic chemistry. 2026; doi:10.1021/acs.joc.6c01011.
APA
Jin Zhao, Yuan-Yuan Fan, Zhong-Chen Huang, Jia-Qian Zhang, Pei-Wen Qiu, Wan-Yun Huang, et al (2026). {"_":"Regioselective Oxyamination Cyclization of Alkynyl-Tethered Indoles to Prepare Functionalized δ-Carboline -Oxides.","i":["N"]}. The Journal of organic chemistry. https://doi.org/10.1021/acs.joc.6c01011
GB/T 7714
Jin Zhao, Yuan-Yuan Fan, Zhong-Chen Huang, Jia-Qian Zhang, Pei-Wen Qiu, Wan-Yun Huang, et al. {"_":"Regioselective Oxyamination Cyclization of Alkynyl-Tethered Indoles to Prepare Functionalized δ-Carboline -Oxides.","i":["N"]}[J]. The Journal of organic chemistry, 2026 doi:10.1021/acs.joc.6c01011.
在 PubMed增强版 阅读全文
翻译全文 · AI 文献问答 · PDF 原文下载 · 引用导出