Uncatalyzed and solvent-free process for the synthesis of 1,4-diarylquinoline derivatives

Synthetic Communications

Volumn 38, Issue 9, 2008, Pages 1355-1364

  Wang, Xiang Shan ^a,b   Zhang, Mei Mei ^b   Jiang, Hong ^b   Yao, Chang Sheng ^a   Tu, Shu Jiang ^a,b  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

1,4 Diarylquinoline; Malononitrile; Solvent free; Synthesis

Indexed keywords

1,4 DIARYLQUINOLINE DERIVATIVE; 2 AMINO 1 (3 CHLORO 4 FLUOROPHENYL) 1 (3 CHLORO 4 FLUOROPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 1 (3 CHLORO 4 FLUOROPHENYL) 4 (2,3 DIMETHOXYLPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 1 (3 CHLORO 4 FLUOROPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 4 (3 NITROPHENYL) 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 1 (3 CHLORO 4 FLUOROPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 4 (4 METHOXYLPHENYL) 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 1 (3 CHLORO 4 FLUOROPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 4 (4 METHYLPHENYL) 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 1 (3 CHLORO 4 FLUOROPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 5 OXO 4 (2 METHOXYLPHENYL)QUINOLINE 3 CARBONITRILE; 2 AMINO 1 (3 CHLORO 4 FLUOROPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 5 OXO 4 PHENYL QUINOLINE 3 CARBONITRILE; 2 AMINO 1,4 DIARYL 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 4 (2 CHLOROPHENYL) 1 (3 CHLORO 4 FLUOROPHENYL) 7,7 DIMETHYL 1,4,5,6,7,8 HEXAHYDRO 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 4 (2 CHLOROPHENYL) 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 4 (2,3 DIMETHOXYLPHENYL) 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 4 (3 CHLOROPHENYL) 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 4 (2 METHOXYLPHENYL) 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 4 (3 NITROPHENYL) 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 4 (4 METHOXYLPHENYL) 5 OXO 4 PHENYL QUINOLINE 3 CARBONITRILE; 2 AMINO 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 4 (4 METHYLPHENYL) 5 OXO QUINOLINE 3 CARBONITRILE; 2 AMINO 7,7 DIMETHYL 1 (4 FLUOROPHENYL) 1,4,5,6,7,8 HEXAHYDRO 5 OXO 4 PHENYL QUINOLINE 3 CARBONITRILE; 3 ARYLAMINO 5,5 DIMETHYLCYCLOHEX 2 ENONE; ALDEHYDE; CYCLOHEXANONE DERIVATIVE; MALONODINITRILE; NITRILE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS;

EID: 42149185072     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801916397     Document Type: Article

References (18)

1. (a) Metzger, J. O. Solvent-free organic syntheses. Angew. Chem. Int. Ed. 1998, 37, 2975-2978;
2. (b) Li, C.-J.; Chan, T.-H. Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 1999, 55, 11149-11176.
3. (a) Loh, T.-P.; Huang, J.-M.; Goh, S.-H.; Vittal, J. J. Aldol reaction under solventfree conditions: Highly stereoselective synthesis of 1,3-amino alcohols. Org. Lett. 2000, 2, 1291-1294;
4. 3. Synth. Commun. 2007, 37, 849-858;
5. (c) Lamiri, M.; Bougrin, K.; Daou, B.; Soufiaoui, M.; Nicolas, E.; Giralt, E. Microwave-assisted solvent-free regiospecific synthesis of 5-alkylidene and 5-arylidenehydantoins. Synth. Commun. 2006, 36, 1575-1584;
6. (d) Koshkin, A. V.; Fedorova, O. A.; Lokshin, V.; Guglielmetti, R.; Hamelin, J.; Texier-Boullet, F.; Gromov, S. P. Microwave-assisted solvent-free synthesis of the substituted spiroindolino naphth[2,1-b][1,4]oxazines. Synth. Commun. 2004, 34, 315-322;
7. (e) Sharifi, A.; Mirzaei, M.; Reza Naimi-Jamal, M. Mild and solvent-free alkynylation of ketones on the KF/alumina. Synth. Commun. 2005, 35, 1039-1044.
8. Beagley, P.; Blackie, M. A. L.; Chibale, K.; Clarkson, C.; Meijboom, R.; Moss, J. R.; Smith, P.; Su, H. Synthesis and antiplasmodial activity in vitro of new ferrocene-chloroquine analogues. Dalton Trans. 2003, 3046-3051.
9. 2 receptor incorporating 4-(2-picolyloxy)-quinoline and 1-(2-picolyl)benzimidazole frameworks. J. Med. Chem. 2004, 47, 2853-2863.
10. Ma, Z.; Hano, Y.; Nomura, T.; Chen, Y. Novel quinazoline-quinoline alkaloids with cytotoxic and DNA topoisomerase II inhibitory activities. Bioorg. Med. Chem. Lett. 2004, 14, 1193-1196.
11. Denton, T. T.; Zhang, X.; Cashman, J. R. 5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6. J. Med. Chem. 2005, 48, 224-239.
12. Fokialakis, N.; Magiatis, P.; Chinou, L.; Mitaku, S.; Tillequin, F. Megistoquinones I and II, two quinoline alkaloids with antibacterial activity from the bark of Sarcomelicope megistophylla. Chem. Pharm. Bull. 2002, 50, 413-414.
13. Fossa, P.; Mosti, L.; Menozzi, G.; Marzano, C.; Baccichetti, F.; Bordin, F. Novel angular furo and thieno-quinolinones: Synthesis and preliminary photobiological studies. Bioorg. Med. Chem. 2002, 10, 743-751.
14. 1-(7-chloro-4-quinolyl)-1,4-bis(3- aminopropyl)piperazine derivatives. J. Med. Chem. 2003, 46, 542-557.
15. Morgan, L. R.; Jursic, B. S.; Hooper, C. L.; Neumann, D. M.; Thangaraj, K.; Leblanc, B. Anticancer activity for 4,4′-dihydroxybenzophenone-2,4- dinitrophenylhydrazone (A-007) analogues and their abilities to interact with lymphoendothelial cell surface markers. Bioorg. Med. Chem. Lett. 2002, 12, 3407-3411.
16. (a) Wang, X. S.; Zhang, M. M.; Shi, D. Q.; Tu, S. J.; Wei, X. Y.; Zong, Z. M. A simple and clean procedure for the synthesis of polyhydro acridine and quinoline derivatives: Reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium. Tetrahedron Lett. 2005, 46, 7169-7173;
17. (b) Wang, X. S.; Zhang, M. M.; Jiang, H.; Shi, D. Q.; Tu, S. J.; Wei, X. Y.; Zong, Z. M. An improved and benign synthesis of 9,10-diarylacridin-1,8-dione and indenoquinoline derivatives from 3-arylamino-5,5-dimethylcyclohex-2-enone, arylaldehyde and 1,3-dicarbonyl compound in ionic liquid medium. Synthesis 2006, 4187-4199;
18. 4]: Reactions of arylaldehyde, 3-arylamino-5,5-dimethyl cyclohex-2-enone, and active methylene compounds. Tetrahedron 2007, 63, 4439-4449.