Solvent-free synthesis of polyhydroquinoline and 1,8-dioxodecahydroacridine derivatives through the Hantzsch reaction catalyzed by a natural organic acid: A green method

被引:37
作者
Sehout, Imene [1 ]
Boulcina, Raouf [1 ]
Boumoud, Boudjemaa [1 ]
Boumoud, Taous [1 ]
Debache, Abdelmadjid [1 ]
机构
[1] Univ Freres Mentouri Constantine 1, Fac Sci Exactes, Lab Synth Mol Interets Biol, Constantine, Algeria
关键词
1,8-Dioxodecahydroacridine; ascorbic acid; Hantzsch reaction; polyhydroquinoline; solvent-free conditions; ONE-POT SYNTHESIS; IONIC LIQUID; EFFICIENT; TRIPHENYLPHOSPHINE; DIHYDROPYRIDINES; TEMPERATURE; ACRIDINE;
D O I
10.1080/00397911.2017.1316406
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Solvent-free and high yielding one-pot synthesis of 1,8-dioxodecahydroacridine and polyhydroquinoline derivatives have been described through Hantzsch condensation of various aldehydes, ammonium acetate with cyclic 1,3-dicarbonyl compounds and ethyl acetoacetate in a very simple, efficient, and environmentally benign method using ascorbic acid as a nontoxic organocatalyst.
引用
收藏
页码:1185 / 1191
页数:7
相关论文
共 33 条
[1]  
[Anonymous], PHARM CHEM
[2]  
[Anonymous], Z CHIN J CATAL
[3]  
[Anonymous], J APPL CHEM RES
[4]  
[Anonymous], PHARM RES
[5]  
[Anonymous], 2014, CHEM SCI T
[6]   Vasorelaxing properties of some phenylacridine type potassium channel openers in isolated rabbit thoracic arteries [J].
Berkan, Ö ;
Saraç, B ;
Simsek, R ;
Yildirim, S ;
Sarioglu, Y ;
Safak, C .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (06) :519-523
[7]   Structure-activity relationship for antineoplastic imidazoacridinones: Synthesis and antileukemic activity in vivo [J].
Cholody, WM ;
Horowska, B ;
ParadziejLukowicz, J ;
Martelli, S ;
Konopa, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1028-1032
[8]   Tetrabutylammonium hexatungstate [TBA]2[W6O19]: Novel and reusable heterogeneous catalyst for rapid solvent-free synthesis of polyhydroquinolines via unsymmetrical Hantzsch reaction [J].
Davoodnia, Abolghasem ;
Khashi, Maryam ;
Tavakoli-Hoseini, Niloofar .
CHINESE JOURNAL OF CATALYSIS, 2013, 34 (06) :1173-1178
[9]   Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for the Synthesis of 1,8-Dioxodecahydroacridines Under Solvent-Free Conditions [J].
Davoodnia, Abolghasem ;
Khojastehnezhad, Amir ;
Tavakoli-Hoseini, Niloofar .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (07) :2243-2248
[10]  
Deo S.S., 2014, J CHEM PHARM RES, V6, P888