Bronsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: a facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate

Shen Guanshuo; Zhou Haifeng; Du Peng; Liu Sensheng; Zou Kun; Uozumi Yasuhiro

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Bronsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: a facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate

机译：1,3-Diketones的抗正囊酸催化选择性C-C键裂解：在乳酸水溶液中的4（3H）喹唑啉酮的容易合成

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A facile and green approach was developed for the synthesis of 4(3H)-quinazolinones by using camphorsulfonic acid as a catalyst in an aqueous solution of biodegradable ethyl lactate. Various 2-aryl-, 2-alkyl-, and 2-(4-oxoalkyl)quinazolinones were obtained by cyclization of 2-aminobenzamides with a wide range of acyclic or cyclic 1,3-diketones via C-C bond cleavage in satisfactory to excellent yields.

机译：通过在可生物降解的乙基乳酸盐水溶液中使用樟脑磺酸作为催化剂来开发一种容易和绿色的方法，用于合成4（3H）-Quinazolinons。通过通过CC键裂解的各种无环或环状1,3-二酮环化，通过CC键裂解以优异的产率来环化2-氨基苯胺，通过CC键或环状1,3-二酮环化获得各种2-芳基 - ，2-烷基 - 和2-（4-氧代烷基）喹唑啉酮。。

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来源
《RSC Advances》 |2015年第104期|共6页
作者
Shen Guanshuo; Zhou Haifeng; Du Peng; Liu Sensheng; Zou Kun; Uozumi Yasuhiro;
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作者单位

China Three Gorges Univ Coll Biol &

Pharmaceut Sci Hubei Key Lab Nat Prod Res &

Dev Yichang 443002 Peoples R China;

China Three Gorges Univ Coll Biol &

Pharmaceut Sci Hubei Key Lab Nat Prod Res &

Dev Yichang 443002 Peoples R China;

China Three Gorges Univ Coll Biol &

Pharmaceut Sci Hubei Key Lab Nat Prod Res &

Dev Yichang 443002 Peoples R China;

China Three Gorges Univ Coll Biol &

Pharmaceut Sci Hubei Key Lab Nat Prod Res &

Dev Yichang 443002 Peoples R China;

China Three Gorges Univ Coll Biol &

Pharmaceut Sci Hubei Key Lab Nat Prod Res &

Dev Yichang 443002 Peoples R China;

China Three Gorges Univ Coll Biol &

Pharmaceut Sci Hubei Key Lab Nat Prod Res &

Dev Yichang 443002 Peoples R China;

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正文语种 eng
中图分类化学;
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1. Bronsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: a facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate [J] . Shen Guanshuo, Zhou Haifeng, Du Peng, RSC Advances . 2015,第104期

机译：1,3-Diketones的抗正囊酸催化选择性C-C键裂解：在乳酸水溶液中的4（3H）喹唑啉酮的容易合成
2. Metal- and Oxidant-Free Synthesis of Quinazolinones from beta-Ketoesters with o-Aminobenzamides via Phosphorous Acid-Catalyzed Cyclocondensation and Selective C-C Bond Cleavage [J] . Li Zhongwen, Dong Jianyu, Chen Xiuling, The Journal of Organic Chemistry . 2015,第19期

机译：β-酮酸酯与邻氨基苯甲酰胺通过亚磷酸催化的环缩合和选择性C-C键裂解反应，无金属和无氧化剂地合成喹唑啉酮
3. Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones catalyzed by graphene oxide nanosheets in an aqueous medium: "on-water" synthesis accompanied by carbocatalysis and selective C-C bond cleavage [J] . Kausar Nazia, Roy Indranil, Chattopadhyay Dipankar, RSC Advances . 2016,第27期

机译：在含水介质中催化的石墨烯氧化物纳米液催化的2,3-二氢喹唑啉酮和喹唑啉-4（3H）酮：“水”合成伴有碳催化和选择性C-C键裂解
4. Indium-Catalyzed Synthesis of Esters from 1,3-Diketones and Alcohols via C-C Bond Cleavage [C] . Atsushi Kawata, Kazumi Takata, Yoichiro Kuninobu Symposium on Organometallic Chemistry . 2007

机译：通过C-C键裂解铟催化1,3-二酮和醇的酯合成酯
5. The Synthesis of Hindered Carbon-Carbon Bonds via the Reaction of N-Vinyl Nitrones and Heterocumulenes, and the Selective Protection of 1,3-Diols. [D] . Chando, Katelyn Marie. 2016

机译：通过N-乙烯基硝基和杂枯烯的反应合成受阻碳-碳键，以及1,3-二元醇的选择性保护。
6. A Simple Procedure for C-C Bond Cleavage of Aromatic and Aliphatic Epoxides with Aqueous Sodium Periodate Under Ambient Conditions [O] . Caitlin M. Binder, Darryl D. Dixon, Erik Almaraz, -1

机译：在环境条件下用高碘酸钠水溶液进行芳族和脂族环氧的C-C键裂解的简单程序
7. A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones with Bronsted acid-catalyzed condensation-cyclization reactions of beta-enamino esters and ethyl trifluoropyruvate [O] . Pei Qing-Lan, Cui Bao-Dong, Han Wen-Yong, 2014

机译：用布朗斯台德酸催化的β-烯氨基酯和三氟丙酮酸乙酯的缩合环化反应轻松合成3-羟基-3-（三氟甲基）-1H-吡咯-2（3H）-酮

Bronsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: a facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate

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