Organic reactions in ionic liquids: Ionic liquid-accelerated one-pot synthesis of 2-arylimidazo[1,2-a]pyrimidines

Synthetic Communications

Volumn 35, Issue 13, 2005, Pages 1741-1746

  Xie, Yuan Yuan ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

2 aminopyrimidine; 2 arylimidazo 1,2 a pyrimidine; Ionic liquid; One pot synthesis

Indexed keywords

2 (2 FURANYL)IMIDAZO[1,2 A]PYRIMIDINE; 2 (4 BROMOPHENYL)IMIDAZO[1,2 A]PYRIMIDINE; 2 (4 CHLOROPHENYL)IMIDAZO[1,2 A]PYRIMIDINE; 2 (4 FLUOROPHENYL)IMIDAZO[1,2 A]PYRIMIDINE; 2 (4 METHOXYPHENYL)IMIDAZO[1,2 A]PYRIMIDINE; 2 (4 METHYLPHENYL)IMIDAZO[1,2 A]PYRIMIDINE; 2 PHENYL 3 METHYLIMIDAZO[1,2 A]PYRIMIDINE; 2 PHENYLIMIDAZO[1,2 A]PYRIMIDINE; ALCOHOL; AMINOPYRIMIDINE DERIVATIVE; BENZENE DERIVATIVE; IMIDAZO[1,2 A]PYRIMIDINE DERIVATIVE; IONIC LIQUID; KETONE; ORGANIC SOLVENT; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; LIQUID; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SYNTHESIS;

EID: 22044437659     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200063911     Document Type: Article

References (21)

1. Fisher, J. G.; Straley, J. M. Novel quaternized heterocyclic monoazo dyes. US Patent 3,928,311, Dec. 23, 1975.
2. Craig, L. E. Compositions for a method of whitening fine fabrics. US Patent 2,785,133, Mar. 12, 1957.
3. (a) Revankar, G. R.; Matthews, T. R.; Robins, R. K. Synthesis and antimicrobial activity of certain imidazo[1,2-a]pyrimidines. J. Med. Chem. 1975, 18, 1253;
4. (b) Rival, Y.; Grassy, G.; Taudou, A.; Ecalle, R. Antifungal activity in vitro of some imidazo[1,2-a]pyrimidine derivatives. Eur. J. Med. Chem. 1991, 26, 13.
5. Buu-Hoi, N. P.; Xuong, Ng. D. 8-Azapyrimidazoles. Compt. Rend. 1956, 243, 2090.
6. Rival, Y.; Grassy, G.; Michael, G. Synthesis and antibacterial activity of some imidazo[1,2-a]pyrimidine derivatives. Chem. Pharm. Bull. 1992, 40, 1170.
7. Patra, M.; Mahapatra, S. K.; Dash, B. Derivatives of imidazole. J. Indian Chem. Soc. 1974, 51, 1031.
8. Sundberg, R. J.; Dahlhausen, D. J.; Manikumar, G. Preparation of 2-aryl- and 2-(aryloxylmethyl)imidazo[1,2-a]pyridines and related compounds. J. Heterocyclc. Chem. 1988, 25, 129.
9. Spitzer, W. A. Methods of producing a positive inotropic effect or vasodilation by administration of 2-phenylimidazo pyrimidines and pyrazines. US Patent 4,636,502, Jan. 13, 1987.
10. (a) Welton, T. Room temperature ionic liquids. Solvent for synthesis and catalysis. Chem. Rev. 1999, 99, 2071;
11. (b) Wassercheid, P.; Keim, W. Ionic liquids - New solutions for transition metal catalysis. Angew. Chem. Int. Ed. Engl. 2000, 39, 3773;
12. (c) Sheldon, R. Catalytic reactions in ionic liquids. Chem. Commun. 2001, 2399;
13. (d) Jairton, D.; Roberto, F.; Paulo, A. Z. S. Ionic liquids (molten salts) phase organometallic catalysis. Chem. Rev. 2002, 102, 3667;
14. (e) Zhao, D.; Wu, M.; Kou, Y.; Min, E. Ionic liquids: Application in catalysis. Catal. Today 2002, 74, 157;
15. (f) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; VCH Wiley: Weinheim, Germany, 2002.
16. (a) Xie, Y. Y.; Chen, Z. C.; Zheng, Q. G. Organic reactions in ionic liquids: Ionic liquid-accelerated cyclocondensation of α-tosyloxyketones with 2-aminopyridine. Synthesis 2002, 1505;
17. (b) Xie, Y. Y.; Chen, Z. C.; Zheng, Q. G. Organic reactions in ionic liquids: α-Tosyloxylation of ketones. J. Chem. Res., Synop. 2002, 618.
18. (a) Bonhôte, P.; Dias, A. P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Hydrophobic, highly conductive ambient-temperature molten salts. Inorg. Chem. 1996, 35, 1168;
19. (b) Suarez, P. A. Z.; Dillius, J. E. L.; Einloft, S.; de Souza, R. F.; Dopont, J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes. Polyhedron 1996, 15, 1217.
20. Doughty, D. G.; Glover, E. E.; Vaughan, K. D. N-Amination and subsequent oxidation of imidazo[1,2-a]pyrimidines. J. Chem. Soc., Perkin Trans 1 1977, 78.
21. +. J.O. C. USSR 1980, 16, 1285.