One-pot site-selective Sonogashira cross-coupling-heteroannulation of the 2-aryl-6,8-dibromoquinolin-4(1H)-ones: synthesis of novel 6-H-pyrrolo[3,2,1-ij]quinolin-6-ones

Malose J. Mphahlele; Felix A. Oyeyiola

首页> 外文期刊>Journal of chemical research: reviews and research papers from all branches of chemistry >One-pot site-selective Sonogashira cross-coupling-heteroannulation of the 2-aryl-6,8-dibromoquinolin-4(1H)-ones: synthesis of novel 6-H-pyrrolo[3,2,1-ij]quinolin-6-ones

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One-pot site-selective Sonogashira cross-coupling-heteroannulation of the 2-aryl-6,8-dibromoquinolin-4(1H)-ones: synthesis of novel 6-H-pyrrolo[3,2,1-ij]quinolin-6-ones

机译：一锅定点的Sonogashira交叉耦合-2-芳基-6,8-二溴喹啉-4（1H）-的异环合：新型6-H-吡咯并[3,2,1-ij]喹啉-的合成6个

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The 2-aryl-6,8-dibromoquinolin-4(1H)-ones were subjected to site-selective Sonogashira cross-coupling with terminal acetylenes as models for Csp~2-Csp bond formation in the presence of Pd/C-PPh_3 and Cul as catalysts and K_2CO_3 as a base in dioxane to afford the 2-substituted 4-aryl-8-bromo-4H-pyrrolo[3，2，,1-ij]quinolin-6-ones. These were， in turn， subjected to Suzuki-Miyaura cross-coupling with 4-fluorophenylboronic acid as coupling partner to afford the 2-substituted 4,8-diaryl-4H-pyrrolo[3,2,1-ij]quinolin-6-ones.

机译：在Pd / C-PPh_3和Pd / C-PPh_3存在的情况下，对2-芳基-6,8-二溴喹啉4（1H）-one与末端乙炔进行位点选择性Sonogashira交叉偶联，作为Csp〜2-Csp键形成的模型。在二恶烷中以Cul为催化剂，以K_2CO_3为碱，得到2-取代的4-芳基-8-溴-4H-吡咯并[3，2，，1-ij]喹啉-6-。然后，将它们依次与4-氟苯基硼酸作为偶联伴侣进行Suzuki-Miyaura交叉偶联，得到2-取代的4,8-二芳基-4H-吡咯并[3,2,1-ij]喹啉-6-那些。

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《Journal of chemical research: reviews and research papers from all branches of chemistry》 |2014年第9期|共4页
作者
Malose J. Mphahlele; Felix A. Oyeyiola;
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正文语种 eng
中图分类化学;
关键词
2-aryl-6; 8-dibromoquiiolin-4(1H)-ones; Sonogashira cross-coupling; 2; 4-diaryl-8-bromo-4H-pyrrolo3; 2; 1-ij quinolin-6-ones; Suzuki-Miyaura cross-coupling; 2; 4; 8-triary1-6H-pyrrolo3; 2; 1-ijquinolin-6-ones;

机译：2-芳基-6;8-二溴喹啉-4（1H）-ones;Sonogashira交叉偶联;2;4-二芳基-8-溴-4H-吡咯并[3;2;1-ij]喹啉-6-ones;铃木宫浦交叉偶联;2;4;8-triary1-6H-pyrrolo [3;2;1-ij] quinolin-6-ones;

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1. One-pot site-selective Sonogashira cross-coupling-heteroannulation of the 2-aryl-6,8-dibromoquinolin-4(1H)-ones: synthesis of novel 6-H-pyrrolo[3,2,1-ij]quinolin-6-ones [J] . Malose J. Mphahlele, Felix A. Oyeyiola Journal of chemical research: reviews and research papers from all branches of chemistry . 2014,第9期

机译：一锅定点的Sonogashira交叉耦合-2-芳基-6,8-二溴喹啉-4（1H）-的异环合：新型6-H-吡咯并[3,2,1-ij]喹啉-的合成6个
2. Unexpected ring-closure products derived from 3-(2-allylanilino)-3-phenylacrylate esters: crystal and molecular structures of 3-acetyl-8-allyl-6-methyl-2-phenylquinolin-4-yl acetate and (2RS)-2,8-dimethyl-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1 -ij]quinolin-6-one [J] . Adriana L. Luque, Carlos M. Sanabria, Alirio Palma, Acta crystallographica. Section C, Structural chemistry. . 2016,第8期

机译：意外的圈封闭产品衍生自3-（2-烯丙基硅氧烷）-3-苯基丙烯酸酯：3-乙酰基-8-烯丙基-6-甲基-2-苯基喹啉-4-基（2rs）的晶体和分子结构 - 2,8-二甲基-4-苯基-1,2-二氢-6H-Pyrrolo [3,2,1-j]喹啉-6-一
3. Unexpected ring-closure products derived from 3-(2-allylanilino)-3-phenylacrylate esters: crystal and molecular structures of 3-acety1-8-allyl6-methyl-2-phenylquinolin-4-yl acetate and (2RS)-2,8-dimethyl-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinolin-6-one [J] . Luque Adriana L., Sanabria Carlos M., Palma Alirio, Acta crystallographica. Section F, Structural biology communications . 2016,第8期

机译：意外的圈闭产品衍生自3-（2-烯丙基硅基）-3-苯基丙烯酸酯：3-ACETA1-8-烯丙基-2-苯基喹啉-4-基醋酸酯的晶体和分子结构，（2RS）-2， 8-二甲基-4-苯基-1,2-二氢-6H-Pyrrolo [3,2,1-IJ]喹啉-6-一
4. ONE-POT MULTICOMPONENT SYNTHESIS of 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES USING SILICA-SUPPORTED PREYSSLER NANOPARTICLES AS A NOVEL, ECO-FRIENDLY and GREEN CATALYST [C] . Fatemeh F. Bamoharram, Majid M. Heravi, Mina Roshani, 6th international conference on environmental catalysis : Abstract book . 2010

机译：一键多组分合成3,4-二氢吡啶酮N-2（1H）-使用二氧化硅支撑的PreySSLer纳米粒子作为新型，环保和绿色催化剂
5. One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation [O] . Fa-Jie Chen, Zhenguo Hua, Jianhui Chen, 2020

机译：通过Sonogashira偶联和氢卤化的级联（Z）-β-卤代苯基酮的单壶合成
6. 2-ARYL-6,8-Dibromoquinolinones as synthons for the synthesis of Polysubstituted 4-ARYL-6-Oxopyrrolo 3,2,1-ij Quinolines [O] . Oyeyiola Felix Adetunji 2015

机译：2-aRYL-6,8-二溴喹啉酮作为合成多取代4-aRYL-6-氧代吡咯并3,2,1-ij喹啉的合成子

One-pot site-selective Sonogashira cross-coupling-heteroannulation of the 2-aryl-6,8-dibromoquinolin-4(1H)-ones: synthesis of novel 6-H-pyrrolo[3,2,1-ij]quinolin-6-ones

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