Efficient and facile synthesis of 3-amino-1-aryl-9h-fluorene-2,4- dicarbonitrile under solvent-free conditions

Synthetic Communications

Volumn 39, Issue 19, 2009, Pages 3493-3499

  Rong, Liangce ^a,b   Han, Hongxia ^a   Jiang, Hong ^b   Tu, Shujiang ^a,b  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Fluorene; Grinding; Multicomponent reactions; Solvent free; Synthesis

Indexed keywords

3 AMINO 1 (2 CHLOROPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (2,4 DICHLOROPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (3 CHLOROPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (3,4 DICHLOROPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (3,4 DIMETHOXYPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (4 BROMOPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (4 CHLOROPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (4 FLUOROPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 (4 METHOXYPHENYL) 9H FLUORENE 2,4 DICARBONITRILE; 3 AMINO 1 4 TOLYL 9H FLUORENE 2,4 DICARBONITRILE; ALDEHYDE; FLUORENE DERIVATIVE; INDANONE DERIVATIVE; MALONONITRILE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENVIRONMENTAL TEMPERATURE; INFRARED SPECTROSCOPY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 70349221566     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902779298     Document Type: Article

References (16)

1. Anastas, P.; Williamson, T. Green Chemistry: Frontiers in Benign Chemical Synthesis and Procedure; Oxford Science Publications, New York, 1998.
2. Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025-1074.
3. Hulme, C.; Gore, V. Multi-component reactions: Emerging chemistry in drug discovery from xylocain to crixivan. Curr. Med. Chem. 2003, 10, 51-80
4. Orru RVA, de Greef M, Recent advances in solution-phase multicom-ponent methodology for the synthesis of heterocyclic compounds. Synthesis 2003, 1471-1499
5. Domling, A.; Ugi, I. Multicomponent reactions with isocyanides. Angew. Chem., Int. Ed. 2000, 39, 3168-3220
6. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes. Acc. Chem. Res. 2003, 36, 899-907
7. Zhu, J. Recent developments in the isonitrile-based multicom-ponent synthesis of heterocycles. Eur. J. Org. Chem. 2003, 7, 1133-1144
8. Domling, A. Recent advances in isocyanide-based multicomponent chemistry. Curr. Opin. Chem. Biol. 2002, 6, 306-313.
9. Rong, L. C.; Li, X. Y.; Wang, H. Y.; Shi, D. Q.; Tu, S. J. An efficient and facile synthesis of 2-amino-4,6-diarylbenzene-1,3-dicarbonitrile and 1,2-dihydro-2-oxo-4,6-diaryl-pyridine-3-carbonitrile under solvent-free conditions. Chem. Lett. 2006, 35, 1314-1315
10. Rong, L. C.; Wang, H. Y.; Shi, J. W.; Yang, F.; Yao, H.; Tu, S. J.; Shi, D. Q. An efficient and facile procedure for the synthesis of 4,6-diaryl-2(1h)-pyridones under solvent-free conditions. J. Heterocyclic Chem. 2007, 44 (10), 1505-1508 (Pubitemid 351225792)
11. Rong, L. C.; Han, H. X.; Yang, F.; Yao, H.; Jiang, H.; Tu, S. J. An efficient one-pot synthesis of 2-amino-4,6-diarylbenzene-1,3-dicarbonitrile under solvent-free conditions. Synth. Commun. 2007, 37 (21), 3767-3772. (Pubitemid 47613507)
12. Ishihara, T.; Kakuta, H.; Moritani, H.; Ugawa, T.; Sakamoto, S.; Tsukamoto, S. I.; Yanagisawa, I. Syntheses and biological evaluation of novel quinuclidine derivatives as squalene synthase inhibitors. Bioorg. Med. Chem. 2003, 11, 2403-2414.
13. Skalova, L.; Nobilis, M.; Szotakova, B.; Kondrova, E.; Savlik, M.; Wosol, V.; Pichard, G. L.; Maser, E. Carbonyl reduction of the potential cytostatic drugs benfluron and 3,9-dimethoxy-benfluron in human in vitro. Biochem. Pharm. 2002, 64, 297-305.
14. Bryant, H. U.; Cullinan, G. J. Preparation of tetrahydrobenzo[a]fluorene compounds for inhibiting bone loss or bone resorption. US patent 5821253 A 13, 1998
15. Chem. Abstr. 1998, 129, 302558.
16. Wang, X. S.; Zhang, M. M.; Li, Q.; Yao, C. S.; Tu, S. J. An improved and clean procedure for the synthesis of one-donor poly-acceptors systems containing 2,6-dicyanoamine moiety in aqueous media catalyzed by TEBAC in the presence and absence of K2CO3. Tetrahedron 2007, 63, 5265-5273.