An efficient procedure for the synthesis of benzimidazole derivatives using Yb(OTf)3 as catalyst under solvent-free conditions

Synthetic Communications

Volumn 34, Issue 23, 2004, Pages 4265-4272

  Wang, Limin ^a   Sheng, Jia ^a   Tian, He ^a   Qian, Changtao ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Benzimidazole; Solvent free reaction; Yb(OTf)3

Indexed keywords

2 ETHYL 5 METHYLBENZIMIDAZOLE; 2 ETHYLBENZIMIDAZOLE; 2 METHYL 5 NITROBENZIMIDAZOLE; 2 METHYLBENZIMIDAZOLE; 2,5 DIMETHYLBENZIMIDAZOLE; 5 CHLOROBENZIMIDAZOLE; 5 METHOXYBENZIMIDAZOLE; 5 METHYLBENZIMIDAZOLE; 5 NITROBENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; BENZOXAZOLE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; YTTERBIUM TRIFLATE;

ARTICLE; CATALYST; SYNTHESIS;

EID: 10644251783     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200039340     Document Type: Article

References (24)

1. Valdez, J.; Cedillo, R.; Campos, A.H.; Yepez, L.; Luis, F.H.; Vazquez, G.N.; Tapia, A.; Cortes, R.; Hernandez, M.; Castillo, R. Synthesis and Antiparasitic Activity of 1H-Benzimidazole Derivatives. Bioorg. Med. Chem. Lett. 2002, 72, 2221-2224.
2. Tanious, F.A.; Hamelberg, D.; Bailly, C.; Czarny, A.; Boykin, D.W.; Wilson, W.D. DNA Sequence Dependent Monomer-Dimer Binding Modulation of Asymmetric Benzimidazole Derivatives. J. Am. Chem. Soc. 2004, 726, 143-153.
3. Fekner, T.; Gallucci, J.; Chan, M.K. Ruffling-Induced Chirality: Synthesis, Metalation, and Optical Resolution of Highly Nonplanar, Cyclic, Benzimidazole-Based Ligands. J. Am. Chem. Soc. 2004, 726, 223-236.
4. (a) Phillips, M.A. The Formation of 2-Substituted Benziminazoles. J. Chem. Soc. 1928, 2393-2399;
5. (b) Hein, D.W.; Alheim, R.J.; Leavitt, JJ. The use of Polyphosphoric Acid in the Synthesis of 2-aryl-and 2-alkyl-Substituted Benzimidazoles, Benzoxazoles and Benzothiazoles. J. Am. Chem. Soc. 1957, 79, 427-429.
6. Hoesl, C.E.; Nefzi, A.; Houghten, R.A. Halogenoalkyl Isocyanates as Bifunctional Reagents in an Aza-Wittig/Heterocyclization Reaction on the Solid Phase: Efficient Entry into New Tetracyclic Benzimidazole Systems. J. Comb. Chem. 2004, 6, 220-223.
7. Bendale, P.M.; Sun, C.-M. Rapid Microwave-Assisted Liquid-Phase Combinatorial Synthesis of 2-(Arylamino)benzimidazoles. J. Comb. Chem. 2002, 4, 359-361.
8. (a) Brain, C.T.; Brunton, S.A. An Intramolecular Palladium-Catalysed Aryl Amination Reaction to Produce Benzimidazoles. Tetrahedron Lett. 2002, 43, 1893-1985;
9. (b) Brain, C.T.; Steer, J.T. An Improved Procedure for the Synthesis of Benzimidazoles Using Palladium-Catalyzed Aryl-Amination Chemistry. J. Org. Chem. 2003, 68, 6814-6816.
10. Evindar, G.; Batey, R.A. Copper- and Palladium-Catalyzed Intramolecular Aryl Guanidinylation: An Efficient Method for the Synthesis of 2-Aminobenzimidazoles. Org. Lett. 2003, 5, 133-136.
11. Dudd, L.M.; Venardou, E.; Garcia-Verdugo, E.; Licence, P.; Blake, A.J.; Wilson, C.; Poliakoff, M. Synthesis of Benzimidazoles in High-Temperature Water. Green Chem. 2003, 5, 187-192.
12. Bougrin, K.; Soufiaoui, M. Nouvelle voie de synthèse des arylimidazoles sous irradiation micro-ondes en "milieu sec". Tetrahedron Lett. 1995, 36, 3683-3686.
13. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W.W.-L. Rare-Earth Metal Triflates in Organic Synthesis. Chem. Rev. 2002, 702, 2227-2302.
14. (a) Ma, Y.; Qian, C.; Wang, L.M.; Yang, M. Lanthanide Triflate Catalyzed Biginelli Reaction One-Pot Synthesis of Dihydropyrimidines under the Solvent-Free Condition. J. Org. Chem. 2000, 65, 3864;
15. (b) Chen, R.; Qian, C.; Vries, J.G.; Sun, P.P.; Wang, L.M. Asymmetric Catalytic Epoxidation of Enones by Chiral Binaphthol-Derived Lanthanum Catalyst. Chinese Journal of Chemistry 2001, 79, 1225;
16. 3 Catalyzed Three-Component Condensation Reaction: A Convenient Synthesis of N,N-Dialkyl-α-Cyanoamines. Synth. Commun. 2002, 32, 2973;
17. (d) Wang, L.M.; Qian, C.; Tian, H.; Ma, Y. Lanthanide Triflate Catalyzed One-Pot Synthesis of Dihydropyrimidin-2(1H)-thiones by a Three-Component of 1,3-Dicarbonyl Compounds, Aldehydes, and Thiourea Using a Solvent-Free Biginelli Condensation. Synth. Commun. 2003, 33, 1459;
18. 3 Catalyzed One-Pot Synthesis of Quinazolin-4(3H)-ones from anthranilic acid, amine, and orthoesters (or formic acid) in Solvent-Free Conditions. Synthesis 2003, 8, 1241;
19. (f) Wang, L.M.; Liu, J.J.; Tian, H.; Qian, C. Ytterbium Triflate Catalyzed Heterocyclization of 1,2-Phenylenediamines and Alkyl oxalates under Solvent-Free Conditions via Phillips Reaction: A Facile Synthesis of Quinoxaline-2,3-diones derivatives. Synth. Commun. 2004, 34, 1.
20. Rabiger, D.J.; Joullié, M.M. The Ionization Constants, Ultraviolet and Infrared Spectra of Some Substituted Benzimidazoles. J. Org. Chem. 1964, 29, 476-482.
21. Green, H.; Day, A.R. The Tautomeric Character of the Imidazole Ring. J. Am. Chem. Soc. 1942, 64, 1167-1173.
22. Murray, M.; Ryan, A.J.; Little, P.J. Inhibition of Rat Hepatic Microsomal Aminopyrine N-Demethylase Activity by Benzimidazole Derivatives. Quantitative Structure-Activity Relationships. J. Med. Chem. 1982, 25, 887-892.
23. Rabinowitz, J.L.; Wagner, B.C. Restriction of Tautomerism in the Amidine System by Hedrogen Bonding. The Case of 4(7)-Nitrobenzimidazole. J. Am. Chem. Soc. 1951, 73, 3030-3037.
24. Bredereck, H.; Simchen, G.; Kantlehner, W. Reaktionen Von Dimethylamino-alkoxy-acetonitrilen. Chem. Ber. 1971, 104, 932-940.