Direct Oxidative Conversion of Benzoyl Chlorides to 2-Imidazoles Using Heteropolyacids

Synthetic Communications

Volumn 39, Issue 17, 2009, Pages 3119-3125

  Sadjadi, Samaheh ^a   Heravi, Majid M ^a   Poormohammad, Nargess ^a   Oskooie, Hossein A ^a   Beheshtiha, Yahya Sh ^a   Bamoharram, Fatemeh F ^b  

^a ALZAHRA UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Heteropolyacids; Imidazole; Recyclable catalysts

Indexed keywords

2 IMIDAZOLE DERIVATIVE; BENZOYL CHLORIDE DERIVATIVE; CHLORIDE; ETHYLENEDIAMINE; HETEROPOLYACID DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 68749095932     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902730978     Document Type: Article

References (14)

1. Laufer, S. A.; Wagner, G. K.; Kotschenreuther, D. A.; Albrecht, W. Novel substituted pyridinyl imidazoles as potent anticytokine agents with low activity against hepatic cytochrome P450 enzymes. J. Med. Chem. 2003, 46, 3230.
2. 3-receptor histamine antagonists. J. Med. Chem. 1996, 39, 3806.
3. Porcari, A. R.; Devivar, R. V.; Kucera, S. L.; Drach, J. C.; Townsend, L. B. Design, synthesis, and antiviral evaluations of 1-(substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole. J. Med. Chem. 1998, 41, 1252.
4. Kim, J. S.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. Substituted 2,5′-bi-1H-benzimidazoles: Topoisomerase I inhibition and cytotoxicity. J. Med. Chem. 1996, 39, 992.
5. Voss, M. E.; Beer, C. M.; Mitchell, S. A.; Blomgren, P. A.; Zhichkin, P. E. A simple and convenient one-pot method for the preparation of heteroaryl-2-imidazoles from nitriles. Tetrahedron 2008, 64, 645.
6. Sharma, S.; Gangal, S.; Rauf, A. Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles, and imidazoles and evaluation of their in vitro antibacterial and antifungal activities. Eur. J. Med. Chem. (in press).
7. 2 system and its application to palladium-catalyzed Mizoroki-Heck reaction. Tetrahedron 2007, 63, 2414.
8. Heravi, M. M.; Derikvand, B. F. F. Highly efficient, four-component, one-pot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts. J. Mol. Catal. A: Chem. 2007, 263, 112.
9. Heravi, M. M.; Sadjadi, S.; Oskooie, H. A.; Hekmat Shoar, R.; Bamoharram, F. F. Heteropolyacids as heterogeneous and recyclable catalysts for the synthesis of benzimidazoles. Catal. Commun. 2008, 9, 504.
10. 40]-catalyzed one-pot synthesis of polyhydroquinoline derivatives via the Hantzsch three-component condensation. J. Mol. Catal. A: Chem. 2007, 264, 50.
11. 40. J. Mol. Catal. A: Chem. 2006, 249, 1.
12. Heravi, M. M.; Zadsirjan, V.; Bakhtiari, K.; Oskooie, H. A.; Bamoharram, F. F. Green and reusable heteropolyacid catalyzed oxidation of benzylic, allylic, and aliphatic alcohols to carbonyl compounds. Catal. Commun. 2007, 8, 315.
13. 40. Bioorg. Med. Chem. Lett. 2007, 17, 3305.
14. Heravi, M. M.; Sadjadi, S.; Oskooie, H. A.; Hekmat Shoar, R.; Bamoharram, F. F. The synthesis of coumarin-3-carboxylic acids and 3-acetylecoumarins derivatives using heteropolyacids as heterogeneous and recyclable catalysts. Catal. Commun. 2008, 9, 470.