Fast and Green Synthesis of 3-Cyano-8-Methyl-2-Oxo-4-Substituted 1,2,5,6,7,8-Hexahydroquinolines

被引：2

作者：

Faidallah, Hassan M. ^{[1
]}

Al-Juaid, Salih S. ^{[1
]}

机构：

[1] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia

来源：

CHEMISTRY AND TECHNOLOGY OF FUELS AND OILS | 2014年 / 50卷 / 03期

关键词：

hexahydroquinoline; ultrasound; BIOLOGICAL EVALUATION; ANTIAMEBIC ACTIVITY; TETRAHYDROQUINOLINE DERIVATIVES; ANTIPROLIFERATIVE ACTIVITY; SULFONAMIDE MOIETY; ANTITUMOR AGENTS; COMPLEXES; THIOSEMICARBAZONES; CYTOTOXICITY; QUINOLINES;

D O I：

10.1007/s10553-014-0516-2

中图分类号：

TE [石油、天然气工业]; TK [能源与动力工程];

学科分类号：

0807 ; 0820 ;

摘要：

Ultrasound was used to synthesis 3-cyano-8-methyl-2-oxo-4-substituted 1,2,5,6,7,8-hexahydroquinolines in a one-pot multicomponent reaction of the corresponding aldehyde, 2-methylcyclohexanone, and excess ammonium acetate and ethyl cyanoacetate in boiling ethanol. The proposed method is uncomplicated, does not take much time, and provides higher product yield, in contrast to the conventional two-step synthesis involving formation of 2-arylidene-6-methylcyclohexanones via Claisen-Schmidt condensation followed by cyclocondensation with ethyl cyanoacetate and ammonium acetate. The structure of the synthesized compounds was confirmed by IR, H-1 and C-13 NMR spectroscopy and x-ray diffraction.

引用

页码：240 / 247

页数：8

共 30 条

[1]

Abadi AH, 2003, ARZNEIMITTEL-FORSCH, V53, P655

[2] Synthesis and antiamoebic activity of metronidazole thiosemicarbazone analogues [J].

Abid, Mohammad ;

Agarwal, Subhash M. ;

Azam, Amir .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (09) :2035-2039

[3] Oxidation of antiparasitic 2-substituted quinolines using metalloporphyrin catalysts: scale-up of a biomimetic reaction for metabolite production of drug candidates [J].

Akagah, Bernardin ;

Lormier, Anh Tuan ;

Fournet, Alain ;

Figadere, Bruno .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (24) :4494-4497

[4] 3-methyl-2-(4-substituted phenyl)-4,5-dihydronaphtho[1,2-c]-pyrazoles:: synthesis and in-vitro biological evaluation as antitumour agents [J].

Al-Saadi, Mohamed S. ;

Rostom, Sherif. A. F. ;

Faidallah, Hassan M. .

ARCHIV DER PHARMAZIE, 2008, 341 (03) :181-190

[5] Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents [J].

Alqasoumi, Saleh I. ;

Al-Taweel, Areej M. ;

Alafeefy, Ahmed M. ;

Ghorab, Mostafa M. ;

Noaman, Eman .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (05) :1849-1853

[6] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].

Cave, GWV ;

Raston, CL ;

Scott, JL .

CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169

[7] Convenient synthesis of 1,2,3,4-tetrahydroquinolines via direct intramolecular reductive ring closure [J].

Chen, Wuhong ;

Liu, Bo ;

Yang, Chunhao ;

Xie, Yuyuan .

TETRAHEDRON LETTERS, 2006, 47 (40) :7191-7193

[8] Synthesis and antiproliferative activity of 2,6-dibenzylamino-3,5-dicyanopyridines on human cancer cell lines [J].

Cocco, MT ;

Congiu, C ;

Lilliu, V ;

Onnis, V .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (12) :1365-1372

[9] Cyanoacetic acid hydrazones of 3-(and 4-)acetylpyridine and some derived ring systems as potential antitumor and anti-HCV agents [J].

El-Hawash, SAM ;

Wahab, AEA ;

El-Demellawy, MA .

ARCHIV DER PHARMAZIE, 2006, 339 (01) :14-23

[10]

El-Sayed O. A., 2009, EUR J MED CHEM, V44, P4637

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