Rare-earth metal chlorides as efficient catalysts for the simple and green synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles under ultrasound irradiation

Synthetic Communications

Volumn 42, Issue 3, 2012, Pages 328-336

  Zhang, Li Jun ^a   Xia, Jing ^a   Zhou, Yong Qing ^a   Wang, Hua ^a   Wang, Shao Wu ^a  

^a ANHUI NORMAL UNIVERSITY   (China)

Author keywords

Benzimidazole; Benzothiazole; Catalysis; Rare earth metal; Ultrasound

Indexed keywords

1 BENZYL 2 PHENYL 1H BENZIMIDAZOLE; 1 BUTYL 2 PROPYL 1H BENZIMIDAZOLE; 1 DIDEUTERATEDBENZYL 2 PHENYL 1H BENZIMIDAZOLE; 1 HEXYL PENTYL 1H BENZIMIDAZOLE; 2 PHENYLBENZOTHIAZOLE; 2 PROPYL 2,3 DIHYDROBENZOTHIAZOLE; 2 TERT BUTYL 1H BENZIMIDAZOLE; ACTIVATED CARBON; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; CHLORIDE; IODINE; LANTHANIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; ULTRASOUND;

EID: 80054690517     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.524337     Document Type: Article

References (36)

1. Wang, R.; Lu, X. X.; Yu, X. Q.; Shi, L.; Sun, Y. Acid-catalyzed solvent-free synthesis of 2-arylbenzimidazoles under microwave irradiation. J. Mol. Cat. A: Chem. 2007, 266, 198-201;
2. Ge, F. L.; Wang, Z. X.; Wan, W.; Lu, W. C.; Hao, J. One-pot synthesis of 2-trifluoromethyl and 2-difluoromethyl substituted benzo-1,3-diazoles. Tetrahedron Lett. 2007, 48, 3251-3254; (Pubitemid 46527749)
3. Zhang, Z. H.; Yin, L.; Wang, Y. M. An expeditious synthesis of benzimidazole derivatives catalyzed by Lewis acids. Catal. Commun. 2007, 8, 1126-1131;
4. Manas, C.; Ajanta, M.; Ratna, M.; Shiho, A.; Yoshihir, H. A Keggin heteropoly acid as an efficient catalyst for an expeditious, one-pot synthesis of 1-methyl-2-(hetero) arylbenzimidazoles. Tetrahedron Lett. 2007, 48, 5239-5242;
5. Lin, S. N.; Yang, L. H. A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Tetrahedron Lett. 2005, 46, 4315-4319;
6. Pranjal, G.; Dilip, K. An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water. Tetrahedron Lett. 2006, 47, 79-82.
7. Yang, X. P.; Jones, R. A.; Lai, R. J.; Waheed, A.; Oye, M. M.; Holmes, A. L. Supramolecular assembly of nanometer-sized heterobimetallic 3d-4f complexes formed with benzimidazole based N,O-donor ligands. Polyhedron 2006, 25, 881-887;
8. Kokare, N. D.; Sangshetti, J. N.; Shinde, D. B. One-pot efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-triaryl-1H- imidazoles using oxalic acid catalyst. Synthesis 2007, 18, 2829;
9. Yadav, J. S.; Subba, R. B. V.; Premalatha, K.; Shiva, S. K. Bismuth(III)-catalyzed rapid and highly efficient synthesis of 2-aryl-1-arylmethyl-1Hbenzimidazoles in water. Can. J. Chem. 2008, 86, 124-128. (Pubitemid 351272766)
10. Varala, R.; Nasreen, A.; Enugala, R.; Adapa, S. R. l-Proline-catalyzed selective synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles. Tetrahedron Lett. 2007, 48, 69-72.
11. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Otokeshb, S.; Baghbanzadehb, M. Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles in water at ambient temperature. Tetrahedron Lett. 2006, 47, 2557-2560. (Pubitemid 43383939)
12. 2. Tetrahedron Lett. 2009, 50, 1495-1497.
13. Zhang, H. H.; Zhou, Z. Q.; Yao, Z. G.; Xu, F.; Shen, Q. Efficient synthesis of pyrimidinone derivatives by ytterbium chloride-catalyzed Biginelli-type reaction under solventfree conditions. Tetrahedron Lett. 2009, 50, 1622-1624;
14. Feng, S. E.; Xu, F.; Shen, Q. An efficient synthesis of 1,5-benzodiazepine derivatives by lanthanide trichloride-catalyzed condensation of o-phenylenediamine with a,b-unsaturatedketone under mild conditions. Chin. J. Chem. 2008, 26, 1163-1167;
15. Xu, F.; Luo, Y. Q.; Wu, J. T.; Shen, Q.; Chen, H. Facile one-pot synthesis of α-amino phosphonates using lanthanoid chloride as catalyst. Heteroat. Chem. 2006, 17, 389-392;
16. Zhang, Y. K.; Liao, S. J.; Xu, Y.; Yu, D. R.; Shen, Q. Reductive dehalogenation of aryl halides by the nanometric sodium hydride using lanthanide chloride as catalyst. Synth. Commun. 1997, 27, 4327-4334; (Pubitemid 28012890)
17. 2AlOH complexes. Russ. J. Org. Chem. 2006, 42, 1570-1572; (Pubitemid 44749142)
18. Zhang, L. J.; Wang, S. W.; Zhou, S. L.; Yang, G. S.; Sheng, E. H. Cannizzaro-type disproportionation of aromatic aldehydes to amides and alcohols by using either a stoichiometric amount or a catalytic amount of lanthanide compounds. J. Org. Chem. 2006, 71, 3149-3153.
19. Li, Y.; Wang, Y. L.; Wang, J. Y. A simple iodine-promoted synthesis of 2-substituted benzothiazoles by condensation of aldehydes with 2-aminothiophenol. Chem. Lett. 2006, 35, 460-461.
20. Kawashita, Y.; Ueba, C.; Hayashi, M. A simple synthesis of 2-arylbenzothiazoles and its application to palladium-catalyzed Mizoroki-Heck reaction. Tetrahedron Lett. 2006, 47, 4231-4233.
21. Bahrami, K.; Mehdi, K. M.; Naali, F. Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles. J. Org. Chem. 2008, 73, 6835-6837.
22. Blacker, A. J.; Farah, M. M.; Hall, M. I.; Marsden, S. P.; Saidi, O.; Williams, J. M. J. Synthesis of benzazoles by hydrogen-transfer catalysis. Org. Lett. 2009, 11, 2039-2042.
23. Fazaeli, R.; Aliyan, H. A heterogeneous catalyst for efficient and green synthesis of 2-arylbenzothiazoles and 2-arylbenzimidazoles. Appl. Catal. A: Gen. 2009, 353, 74-79.
24. Pratap, U. R.; Mali, J. R.; Jawale, D. V.; Mane, R. A. Bakers' yeast catalyzed synthesis of benzothiazoles in an organic medium. Tetrahedron Lett. 2009, 50, 1352-1354.
25. Ranu, B. C.; Jana, R.; Dey, S. S. An efficient and green synthesis of 2-arylbenzothiazoles in an ionic liquid, [pmIm]Br under microwave irradiation. Chem. Lett. 2004, 33, 274-275. (Pubitemid 38661958)
26. Chhanda, M.; Arup, D. Water-promoted Dowex 50W catalyzed highly efficient green protocol for 2-arylbenzothiazole formation. J. Heterocycl. Chem. 2009, 46, 91-95.
27. Xiao, H. L.; Chen, J. X.; Liu, M. C.; Zhou, D. J.; Ding, J. C.; Wu, H. Y. Trichloroisocyanuric acid (TCCA) as a mild and efficient catalyst for the synthesis of 2-arylbenzothiazoles. Chem. Lett. 2009, 38, 170-171.
28. Hashem, S.; Omid, A.; Tabaei, S. M. H. Simple and mild procedures for synthesis of benzimidazole derivatives using heterogeneous catalyst systems. J. Heterocycl. Chem. 2008, 45, 1293-1298.
29. Manas, C.; Sulakshana, K.; Ajanta, M.; Shiho, A.; Yoshihiro, H. Application of sulfamic acid as an eco-friendly catalyst in an expedient synthesis of benzimidazoles. Heterocycles 2006, 68, 967-974.
30. Chan, S. C.; Jun, U. K. Ruthenium-catalyzed synthesis of benzimidazoles from N-alkyl-1,2-diaminobenzenes via alkyl group transfer. Bull. Kor. Chem. Soc. 2008, 29, 1097-1098.
31. Deng, X. H.; McAllister, H.; Mani, N. S. CuI-catalyzed amination of arylhalides with guanidines or amidines: A facile synthesis of 1-H-2-substituted benzimidazoles. J. Org. Chem. 2009, 74, 5742-5745.
32. Saikat, D. S.; Dilip, K. Practical, ecofriendly, and chemoselective method for the synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using amberlite IR-120 as a reusable heterogeneous catalyst in aqueous media. Synth. Commun. 2009, 39, 980-991.
33. Mikami, K.; Terada, M.; Matsuzawa, H. "Asymmetric" catalysis by lanthanide complexes. Angew. Chem., Int. Ed. 2002, 41, 3554-3571.
34. Billeau, S.; Chatel, F.; Robin, M.; Faure, R.; Galy, J. P. 1Hand 13C chemical shifts for 2-aryl and 2-N-arylamino benzothiazole derivatives. Magn. Reson. Chem. 2006, 44, 102-105.
35. Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Synthesis of 2-arylbenzothiazoles and imidazoles using scandium triflate as a catalyst for both a ring closing and an oxidation steps. Heterocycles 2004, 63, 2769-2783.
36. Russell, G. A.; Wang, L.; Rajaratnam, R. Reductive tert-butylation of anils by tertbutylmercury halides. J. Org. Chem. 1996, 61, 8988-8991. (Pubitemid 127745124)