A Theoretical Study on the Reaction Mechanism of 4-Fluorobenzaldehyde, β-Naphthylamine and Meldrum s Acid One-pot to Form 1-(4-Fluorophenyl)-1,2-Dihydrobenzo[f] Quinolin-3(4H)-one

Acta Chimica Sinica ›› 2010, Vol. 68 ›› Issue (08): 760-768. Previous Articles Next Articles

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4-氟苯甲醛、β-萘胺和Meldrum酸一锅反应生成1-(4-氟苯基)-1,2-二氢苯并[f]喹啉-3(4H)-酮的反应机理理论研究

张福兰*^{,1，张迪²，胡武洪¹，李来才²}

(¹长江师范学院化学化工学院重庆涪陵 408100)
(²四川师范大学化学与材料学院成都 610066)

投稿日期:2009-07-13 修回日期:2009-10-16 发布日期:2009-12-14
通讯作者: 张福兰 E-mail:cjsy0606@163.com

A Theoretical Study on the Reaction Mechanism of 4-Fluorobenzaldehyde, β-Naphthylamine and Meldrum s Acid One-pot to Form 1-(4-Fluorophenyl)-1,2-Dihydrobenzo[f] Quinolin-3(4H)-one

Zhang Fulan*^{,1 Zhang Di² Hu Wuhong¹ Li Laicai²}

(¹College of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling, Chongqing 408100)
(²College of Chemistry and Material Science, Sichuan Normal University, Chengdu 610066)

Received:2009-07-13 Revised:2009-10-16 Published:2009-12-14
Contact: Fu-Lan ZHANG E-mail:cjsy0606@163.com

Abstract

The reaction mechanism of 4-fluorobenzaldehyde, β-naphthylamine and meldrum s acid one-pot to form 1-(4-fluorophenyl)-1,2-dihydrobenzo[f] quinolin-3(4H)-one were studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the B3LYP/6-311G* level. Vibration analysis was carried out to confirm the transition state structure, and the intrinsic reaction coordinate (IRC) method was performed to search the reaction path. In addition, atoms in molecules (AIM) theories were used to discuss bond natures. The reaction in water solution was investigated at the same level with SCRF(PCM) method. Reaction pathways were investigated in this study. The result indicates that the reaction Re→TS1→IM1→TS2→IM2→TS3→IM3→TS4→IM5→TS7→IM9→TS13→ IM10→TS14→P3 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the experiment results.

Key words: 4-fluorobenzaldehyde, β-naphthylamine, meldrum s acid, 1-(4-fluorophenyl)-1,2-dihydro- benzo[f] quinolin-3(4H)-one, reaction mechanism, solvent effects

Cite this article

ZHANG Fu-Lan, ZHANG Di, HU Wu-Hong, LI Lai-Cai. A Theoretical Study on the Reaction Mechanism of 4-Fluorobenzaldehyde, β-Naphthylamine and Meldrum s Acid One-pot to Form 1-(4-Fluorophenyl)-1,2-Dihydrobenzo[f] Quinolin-3(4H)-one[J]. Acta Chimica Sinica, 2010, 68(08): 760-768.

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4-氟苯甲醛、β-萘胺和Meldrum酸一锅反应生成1-(4-氟苯基)-1,2-二氢苯并[f]喹啉-3(4H)-酮的反应机理理论研究

A Theoretical Study on the Reaction Mechanism of 4-Fluorobenzaldehyde, β-Naphthylamine and Meldrum s Acid One-pot to Form 1-(4-Fluorophenyl)-1,2-Dihydrobenzo[f] Quinolin-3(4H)-one

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