Microwave-assisted one-pot synthesis of 2-(substituted phenyl)-1H- benzimidazole derivatives

Synthetic Communications

Volumn 37, Issue 17, 2007, Pages 2815-2825

  Navarrete Vázquez, Gabriel ^a   Moreno Diaz, Hermenegilda ^a   Estrada Soto, Samuel ^a   Torres Piedra, Mariana ^a   León Rivera, Ismael ^a   Tlahuext, Hugo ^a   Muñoz Muñiz, Omar ^b   Torres Gómez, Hector ^a  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MORELOS   (Mexico)

^b UNIVERSIDAD VERACRUZANA   (Mexico)

Author keywords

Benzimidazole; Microwave assisted synthesis; Solvent free reaction

Indexed keywords

1,2 PHENYLENEDIAMINE; 2 (1H BENZIMIDAZOL 2 YL)PHENOL; 2 (2 ETHOXYPHENYL) 1H BENZIMIDAZOLE; 2 (3 HYDROXY 4 METHOXYPHENYL) 1H BENZIMIDAZOLE; 2 (4 METHOXYPHENYL) 1H BENZIMIDAZOLE; 2 (4 METHOXYPHENYL) 5 METHYL 1H BENZIMIDAZOLE; 2 (5 METHYL 1H BENZIMIDAZOL 2 YL)PHENOL; 2 [(5 TRIFLUOROMETHYL) 1H BENZIMIDAZOL 2 YL]PHENOL; 2-(SUBSTITUTED PHENYL)-1H-BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; OXIDIZING AGENT; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; MELTING POINT; MICROWAVE IRRADIATION; REACTION TIME;

EID: 34548439446     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701473325     Document Type: Article

References (14)

1. Navarrete-Vázquez, G.; Yepez-Mulia, L.; Hernández-Campos, A.; Tapia, A.; Hernández-Luis, F.; Cedillo, R.; González, J.; Martínez-Fernández, M.; Martínez-Grueiro, M.; Castillo, R. Synthesis and antiparasitic activity of albendazole and mebendazole analogues. Bioorg. Med. Chem. 2003, 11, 4615-4622.
2. Özden, S.; Atabey, D.; Yildiz, S.; Göker, H. Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5- carboxylates derivatives carrying amide or amidine groups. Bioorg. Med. Chem. 2005, 13, 1587-1597.
3. Andrzejewska, M.; Yépez-Mulia, L.; Cedillo-Rivera, R.; Tapia, A.; Vilpo, L.; Vilpo, J.; Kazimierczuk, Z. Synthesis, antiprotozoal and anticancer activity of substituted 2-trifluoromethyl- and 2-pentafluoroethylbenzimidazoles. Eur. J. Med. Chem. 2002, 37, 973-978.
4. 4 receptor antagonists. Bioorg. Med. Chem. Lett. 2004, 14, 5251-5256.
5. Mavandadi, F.; Lidström, P. Microwave-assisted chemistry in drug discovery. Curr. Top. Med. Chem. 2004, 4, 773-792.
6. Navarrete-Vázquez, G.; Cedillo, R.; Hernández-Campos, A.; Yepez-Mulia, L.; Hernández-Luís, F.; Valdez, J.; Morales, R.; Cortes, R.; Hernandez, M.; Castillo, R. Synthesis and antiparasitic activity of 2-(trifluoromethyl)-benzimidazole derivatives. Bioorg. Med. Chem. Lett. 2001, 11, 187-190.
7. Göker, H.; Ku, C.; Boykin, D. W.; Yildiz, S.; Altanar, N. Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species. Bioorg. Med. Chem. 2002, 10, 2589-2596.
8. Ben-Alloum, A.; Bakkas, S.; Soufiaoui, M. Benzimidazoles: Oxydation hétérocyclisante par le nitrobenzène ou le diméthylsulfoxyde sur silice et sous irradiation micro-ondes ou ultra-violet. Tetrahedron Lett. 1998, 39, 4481-4384.
9. Verner, E.; Katz, B. A.; Spencer, J. R.; Allen, D.; Hataye, J.; Hruzewicz, W.; Hui, H. C.; Kolesnikov, A.; Li, Y.; Luong, C.; Martelli, A.; Radika, K.; Rai, R.; She, M.; Shrader, W.; Sprengeler, P. A.; Trapp, S.; Wang, J.; Young, W. B.; Mackman, R. L. Development of serine protease inhibitors displaying a multicentered short (<2.3 A) hydrogen bond binding mode: Inhibitors of urokinase-type plasminogen activator and factor Xa. J. Med. Chem. 2001, 44, 2753-2771.
10. Lombardy, R. L.; Tanious, F. A.; Ramachandran, K.; Tidwell, R. R.; Wilson, W. D. Synthesis and DNA interactions of benzimidazole dications which have activity against opportunistic infections. J. Med. Chem. 1996, 39, 1452-1462.
11. Lin, S.; Yang, L. A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Tetrahedron Lett. 2005, 46, 4315-4319.
12. Estrada-Soto, S.; Villalobos-Molina, R.; Aguirre-Crespo, F.; Moreno-Díaz, H.; Torres-Piedra, M.; Navarrete-Vázquez, G. Relaxant activity of 2-(substituted phenyl)-1H-benzimidazoles on isolated rat aortic rings: Design and synthesis of 5-nitro derivatives. Life Sci. 2006, 79, 430-435.
13. Navarrete-Vázquez, G.; Moreno-Díaz, H.; Aguirre-Crespo, F.; León-Rivera, I.; Villalobos-Molina, R.; Muñoz-Muñiz, O.; Estrada-Soto, S. Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres. Bioorg. Med. Chem. Lett. 2006, 16, 4169-4173.
14. Moreno-Díaz, H.; Navarrete-Vázquez, G.; Estrada-Soto, S.; Tlahuext, H. 2-(4-Methoxyphenyl)-1H-benzimidazole. Acta Cryst. 2006, E62, o2601-o2602.