由 2,2-二取代吲哚啉-3-酮单锅合成 N-融合喹诺酮-4 四环支架

IF 3.7 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Omega Pub Date : 2024-10-29 DOI:10.1021/acsomega.4c0769110.1021/acsomega.4c07691

Nikolai A. Arutiunov, Anna M. Zatsepilina, Anna A. Aksenova, Nicolai A. Aksenov, Dmitrii A. Aksenov, Alexander V. Leontiev and Alexander V. Aksenov*,

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引用次数: 0

摘要

报告了一种 C2-季吲哚基的级联转化方法，该方法可高效组装复杂的（二氢）吲哚并[1,2-a]喹啉-5-酮环系统。该方法涉及以克为单位制备 2-(2-芳基-3-氧代吲哚啉-2-基)-2-苯基乙腈，然后用甲基酮将其转化为相应的 2-(2-氧代-2-芳基(烷基)乙基)-2-苯基吲哚啉-3-酮。后者可以很高的产率（75-96%）分离出来，或者在邻硝基苯乙酮的情况下，就地用于进一步的碱辅助分子内 SNAr 环化，从而得到吲哚基融合的喹啉酮-4 杂交化合物（高达 95%）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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One-Pot Synthesis of N-Fused Quinolone-4 Tetracyclic Scaffolds from 2,2-Disubstituted Indolin-3-ones

A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly of complex (dihydro)indolo[1,2-a]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation of 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones to the corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. The latter can either be isolated with good yields (75–96%) or, in the case of o-nitroacetophenone, used in situ for further base-assisted intramolecular S_NAr cyclization resulting in indoxyl-fused quinolone-4 hybrids (up to 95%).

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来源期刊

ACS Omega Chemical Engineering-General Chemical Engineering

CiteScore

6.60

自引率

4.90%

发文量

3945

审稿时长

2.4 months

期刊介绍： ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.