One-Pot Synthesis of 9-Aryl-3,6-dimethyl-2,7-dioxa-1,2,7,8,9,10- hexahydro-1,8-acridinedione Derivatives

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Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (06): 1071-1073. Previous Articles Next Articles

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3,6-二甲基-9-芳基-2,7-二氧杂-1,2,7,8,9,10-六氢-1,8-吖啶二酮衍生物的一步合成

刘波，李卓宁，张雪利，吕维中，高原*

(深圳大学化学化工学院深圳 518060)

收稿日期:2006-12-05 修回日期:2007-11-08 发布日期:2008-06-26
通讯作者: 高原

One-Pot Synthesis of 9-Aryl-3,6-dimethyl-2,7-dioxa-1,2,7,8,9,10- hexahydro-1,8-acridinedione Derivatives

LIU Bo, LI Zhuo-Ning, ZHANG Xue-Li, LÜ Wei-Zhong, GAO Yuan*

(College of Chemistry and Chemical Engineering, Shenzhen University, Shenzhen 518060)

Received:2006-12-05 Revised:2007-11-08 Published:2008-06-26

Contact: GAO Yuan

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Abstract

A series of 9-aryl-3,6-dimethyl-2,7-dioxa-1,2,7,8,9,10-hexahydro-1,8-acridinedione derivatives were synthesized by one-pot reaction of substituted benzaldehyde, 4-hydroxyl-6-methyl-2-pyranone with ammonium acetate in acetic acid. The structures of the products were determined by IR, ¹H NMR spectra and elemental analysis. A possible mechanism for this reaction was proposed.

Key words: 4-hydroxyl-6-methyl-2-pyranone, acridinedione, aromatic aldehyde

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LIU Bo, LI Zhuo-Ning, ZHANG Xue-Li, LÜ Wei-Zhong, GAO Yuan*. One-Pot Synthesis of 9-Aryl-3,6-dimethyl-2,7-dioxa-1,2,7,8,9,10- hexahydro-1,8-acridinedione Derivatives[J]. Chin. J. Org. Chem., 2008, 28(06): 1071-1073.

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[1]	Wenxin Zhao, Mengjun Huang, Shengnan Li, Yujing Liu, Zhongqiu Liu, An'guo Ying. One-Pot Synthesis of 3,4-Dihydropyrimidine-2-one Derivatives via Biginelli Reactions Catalyzed by SnCl₂@MNPs [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2743-2749.
[2]	Ren Xinfeng, Song Xiaoping, Ma Yingchao, Li Ya. Method for the Synthesis of 1,1-Dichloroalkenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1388-1393.
[3]	Liu Xu-Bo, Lin Jia-Le, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 663-668.
[4]	Lu Yuhan, Han Yingzhi, Sun Yadong, Abdukader Ablimit, Wang Duozhi, Liu Chenjiang. Application of Iodobenzene Acetate Promoted Oxidation in the Synthesis of 2-Amino-1,3,4-thiadiazole Molecules [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 447-453.
[5]	Yang Xiaojiang, Mao Jincheng, Zhang Heng, Zhang Yang, Mao Jinhua. Copper-Catalyzed Aerobic Oxidation Reaction of Benzyl Alcohol in Water under Base-Free Condition [J]. Chin. J. Org. Chem., 2018, 38(10): 2780-2783.
[6]	Zhang Wenfeng, Xu Zhaohui, Tu Yuanhong, Liao Chuanwen. Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water [J]. Chin. J. Org. Chem., 2017, 37(9): 2449-2453.
[7]	Lin Chunhua, Yuan Jianjun, Liu Deyong, Zhang Houfu, Xu Zhaohui. Efficient Synthesis of 5,5-(Phenylmethylene)bis(2,2-dimethyl-1,3-dioxane-4,6-dione) Derivatives in Biobased Gluconic Acid Aqueous Solution [J]. Chin. J. Org. Chem., 2017, 37(6): 1560-1564.
[8]	Zhang Xun, Yang Nianfa. Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes [J]. Chin. J. Org. Chem., 2017, 37(4): 1027-1032.
[9]	Liu Dacai, Zhu Weijun, Zhang Anlin, Yang Nianfa, Yang Liwen. Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes [J]. Chin. J. Org. Chem., 2015, 35(8): 1797-1801.
[10]	Xu Zhaohui, Lin Chunhua. Solvent-Free Synthesis of 5-Alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones under Ultrasonic Irradiation with CePW₁₂O₄₀ as Catalyst [J]. Chin. J. Org. Chem., 2013, 33(07): 1540-1544.
[11]	Yuan Mingyue, Liu Weihua, Zhang Yingqun, Yan Hongfei, Zhang Dongnuan, Liu Huimin, Wang Jianping. Synthesis and Biological Activity of N-[4-(Coumarin-3-yl)thiazol-2-yl] Aromatic Aldehyde Hydrazones under Microwave Irradiation [J]. Chin. J. Org. Chem., 2013, 33(05): 1108-1112.
[12]	Ren Zhenghong, Li Sheng, Zhang Xinghua, Fan Li, Zhou Guangming, Yang Dacheng. One-Pot Synthesis of N-[3-(4-Methylphenyl)-3-oxo-1-arylpropyl]ace-tamides Employing Trifluoroacetic Acid as an Efficient Catalyst [J]. Chin. J. Org. Chem., 2013, 33(05): 1047-1056.
[13]	Zhou, Jianfeng Lou, Fengwen Sun, Xiaojun An, Litao Zhi, Sanjun Huo, Juanjuan Zheng, Li Wang, Xingshuai. One-Pot Synthesis of 3,3'-(4-arylpyridine-2,6-diyl)-bis (2H-chromen-2-one) Derviatives under Microwave Irradiation [J]. Chin. J. Org. Chem., 2012, 32(06): 1112-1115.
[14]	Deng Lanqing, Xu Zhonghai, Shang Yunfeng, Dai Wenjing, Hu Huimin, Deng Suiping, Ouyang Jianming. A New Synthesis of 2-Amino-4,5-substituted Pyrimidine Derivatives [J]. Chin. J. Org. Chem., 2012, 32(06): 1141-1145.
[15]	You Xinkui, Lin Zhilan, Zhang Xueli, Gao Yuan . Synthesis of 9-Aryl-3-methyl-1,8-dioxo-2,10-dioxanthens [J]. Chin. J. Org. Chem., 2012, 32(01): 156-159.