Selective synthesis of dihydro- and dehydrogenated spirocyclopenta[b]indoles via acid-modulated [3+2] cycloaddition reaction

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2024-11-17 DOI:10.1016/j.molstruc.2024.140792

Dong-Mei Liu , Shao-Cong Zhan , Ren-Jie Fang , Jing Sun , Chao-Guo Yan

引用次数: 0

Abstract

p-TsOH catalyzed [3+2] cycloaddition of 3-benzoylvinylindoles with 3-hydroxy-3-(indol-3-yl)indolin-2-ones in acetonitrile gave functionalized 3,4-dihydrospiro[cyclopenta[b]indole-1,3′-indolin]-2′-ones in good yields and with high diastereoselectivity. In the presence of FeCl_3, the similar reaction of 3-benzoylvinylindoles with 3-hydroxy-3-(indol-3-yl)indolin-2-ones in toluene afforded dehydrogenated spiro[cyclopenta[b]indole-1,3′-indolin]-2′-ones in good yields. On the other hand, p-TsOH catalyzed [3+2] cycloaddition of 3-benzoylvinylindoles and 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones gave 3,4-dihydrospiro[cyclopenta[b]indole-1,2′-indene]-1′,3′-diones, which could be oxidized to dehydrogenated spiro[cyclopenta[b]indole-1,2′-indene]-1′,3′-diones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Abstract Image

查看原文本刊更多论文

通过酸调节 [3+2] 环加成反应选择性合成二氢和脱氢螺环戊并[b]吲哚

p-TsOH 催化 3-苯甲酰乙烯基吲哚与 3-羟基-3-(吲哚-3-基)吲哚啉-2-酮在乙腈中发生 [3+2] 环加成反应，得到了官能化的 3,4-二氢螺[环戊并[b]吲哚-1,3′-吲哚啉]-2′-酮，产率高，非对映选择性强。在 FeCl3 存在下，3-苯甲酰基乙烯基吲哚与 3-羟基-3-(吲哚-3-基)吲哚啉-2-酮在甲苯中发生类似反应，得到脱氢的螺[环戊并[b]吲哚-1,3′-吲哚啉]-2′-酮，产率良好。另一方面，在 p-TsOH 催化下，3-苯甲酰乙烯基吲哚和 2-羟基-2-（吲哚-3-基）-茚-1,3-二酮发生 [3+2] 环加成反应，得到 3,4-二氢螺[环戊并[b]吲哚-1、2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）可将其氧化为脱氢螺[环戊并[b]吲哚-1,2′-茚]-1′,3′-二酮。）

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.