One-Pot Synthesis of 4-(Chromon-3-yl)-3-ethoxylcarbonyl-1,4,5,6,7,8-hexahydro-5-oxo-2,7,7-trimethylquinoline

Abstract

series of new 4-(chromon-3-yl)-3-ethoxylcarbonyl-1,4,5,6,7,8-hexahydro-5-oxo-2,7,7- trimethylquinoline derivatives were synthesized from substituted 3-formylchromones, 5,5-dimethyl-1,3- cyclohexadione, am-monium acetate, and ethyl acetoacetate in a one-pot reaction. The structures of these compounds were characterized. The crystal structure of compound 2f was determined by X-ray single diffraction study, which belongs to monoclinic system with space P2/c and unit cell parameters: a＝2.0255(4) nm, b＝0.9132(2) nm, c＝1.4066(3) nm, β＝121.60(3)°, V＝2.2159(8) nm³, Z＝4, D_c＝1.335 g/cm³, μ＝0.209 mm^－1, F(000)＝736, R₁＝0.0556, wR₂＝0.1248.

Key words: 5,5-dimethyl-1,3-cyclohexadione, 3-formylchromone, hexahydroquinoline, crystal structure

Cite this article

LIU Jun, LIU Gang, TIAN Xiao-Hong, CAO Ling-Hua*. One-Pot Synthesis of 4-(Chromon-3-yl)-3-ethoxylcarbonyl-1,4,5,6,7,8-hexahydro-5-oxo-2,7,7-trimethylquinoline[J]. Chin. J. Org. Chem., 2008, 28(01): 73-77.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[2]	Jing Wang, Linlin Wu, Qian Wang. Synthesis and Characterization of New Indeno[1,2-b]fluorene-6,12-dione Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 223-228.
[3]	Chensheng Yu, Han Wang, Lijing Min, Liang Han, Jianjun Shi, Xinghai Liu. Synthesis, Cyrstal Structure and Fungicidal Activity of New Triazole Compounds Containing Trifluoromethylphenyl Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4498-4503.
[4]	He Mei, He Chaofan, Liu Ling, Ye Jiao, Hu Aixi, Chen Yun, Xu Lujie, Liu Ailin. Synthesis, Crystal Structure and Neuraminidase Inhibitory Activity of 1,2,4-Triazole-3-sulfide Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2402-2410.
[5]	Jia Huijie, Han Limin, Zhu Ning, Gao Yuanyuan, Wang Yaqi, Suo Quanling. A Study on Recognition Property of Acetylferrocenyl Benzothiazole to Al³⁺, Cr³⁺ and Fe³⁺ [J]. Chin. J. Org. Chem., 2019, 39(6): 1753-1760.
[6]	Zhao Bangtun, Fu Huimin, Chen Xiaoji, Zhu Weimin. A New Method for Synthesizing Tetrathiafulvalene Vinylogues [J]. Chin. J. Org. Chem., 2018, 38(8): 2116-2121.
[7]	Shi Juan, Zhang Zunting. Synthesis and Fluorescent Property of Benzo [c]coumarin Carboxylic Derivatives [J]. Chin. J. Org. Chem., 2018, 38(6): 1462-1468.
[8]	Zhang Weijie, Xu Li, Song Jinsheng, Ma Zhiying, Wang Hua. Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties [J]. Chin. J. Org. Chem., 2018, 38(5): 1119-1125.
[9]	Mroz Robert, Vezzu Dileep A. K., Wallace Brian, Ravindranathan Deepak, Carroll Jeffrey, Pike Robert D., Huo Shouquan. A Comparative Study on Phosphorescent Cycloplatinated Complexes Based on Tridentate C^N^N-Coordinating Ligands and Phenylethynyl or Phenyl Ligand [J]. Chin. J. Org. Chem., 2018, 38(1): 171-182.
[10]	Zhang Meimei, Wang Jie, Liu Jianquan, Wang Xiangshan. One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions [J]. Chin. J. Org. Chem., 2017, 37(6): 1565-1570.
[11]	Chen Sufang, Hong Yubiao, Liu Yuanzhong, Xue Mingqiang, Zheng Yu, Shen Qi. Synthesis and Properties of Sodium and Europium(Ⅲ) Cryptates Incorporating the 4,4'-Substituted-2,2'-bipyridine Units [J]. Chin. J. Org. Chem., 2017, 37(5): 1198-1204.
[12]	Zhang Wenlong, Chen Dongmei, Liu Xingli, Huang Chao, Zhu Bixue. Synthesis, Structure and Anion Recognition of Urea-Functionalized Schiff Base Macrocyclic Compound [J]. Chin. J. Org. Chem., 2017, 37(2): 474-479.
[13]	Ou Yaping, Zhang Jing, Yu Jiangxi, Zhu Xiaoming. Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives [J]. Chin. J. Org. Chem., 2017, 37(2): 394-402.
[14]	Ren Yaping, Liu Xu, Wang Rui, Zhou Yuanqing, Li Biao, Xu Yan, Song Maoping. Synthesis and Properties of 4-Ferrocenyl-benzoyl-thiadiazole Derivatives [J]. Chin. J. Org. Chem., 2017, 37(1): 110-115.
[15]	Kang Haixia, Bai Jing, Xi Zhentao, Zhang Manman, Fu Yuqin, Zou Dapeng. Reaction of 5(R)-(l-Menthoxy)-2(5H)-furanone with Diethyl Bromomalonate [J]. Chin. J. Org. Chem., 2016, 36(8): 1915-1920.

4-(色酮-3-基)-3-乙氧羰基-1,4,5,6,7,8-六氢-5-氧代-2,7,7-三甲基喹啉的一步合成