A new method for the synthesis of 2-aryl-1H-benzimidazoles: Selenium-catalyzed reductive N-heterocyclization of benzylidene(2-nitroaryl) amines with carbon monoxide

Synlett

Volumn , Issue 1, 2006, Pages 109-111

  Nishiyama, Yutaka ^a   Fujimoto, Mayu ^a   Sonoda, Noboru ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

2 Aryl 1H benzimidazole; Benzylidene(2 nitroaryl) amine; Carbon monoxide; Selenium

Indexed keywords

2 METHYLBENZYLIDENE (2 NITROPHENYL)AMINE; 3 METHYLBENZYLIDENE (2 NITROPHENYL)AMINE; 4 CHLOROBENZYLIDENE (2 NITROPHENYL)AMINE; 4 CYANOBENZYLIDENE (2 NITROPHENYL)AMINE; 4 METHOXYBENZYLIDENE (2 NITROPHENYL)AMINE; 4 METHYLBENZYLIDENE (2 NITROPHENYL)AMINE; BENZIMIDAZOLE DERIVATIVE; BENZYLIDEN(2 NITROPHENYL)AMINE; BENZYLIDENE DERIVATIVE; CARBON MONOXIDE; SELENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; REDUCTION; SYNTHESIS;

EID: 30544438253     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922771     Document Type: Article

References (13)

1. For recent reviews; see: Grimmett, M. R. Imidazoles and their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry, Vol. 5; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, 457-498.
2. (a) Tolari, S.; Cenini, S.; Crotti, C.; Gianelloy, E. J. Mol. Catal. 1994, 87, 203.
3. (b) Crotti, C.; Cenini, S.; Ragaini, F.; Porta, F.; Tolari, S. J. Mol. Catal. 1992, 72, 283.
4. (c) Watanabe, Y.; Suzuki, N.; Tsuji, Y. Bull. Chem. Soc. Jpn. 1982, 55, 2445.
5. (d) Watanabe, Y.; Takatsuki, K.; Shim, S. C.; Mitsudo, T.; Takegami, Y. Bull. Chem. Soc. Jpn. 1978, 51, 3397.
6. It has already been reported that the reaction of benzylidene(2- nitrophenyl)amine with triethyl phosphite affords 2-phenyl-1H-benzimidazole in 47% yield. See: Cadogan, J. I. G.; Marshall, R.; Smith, D. M.; Todd, M. J. J. Chem. Soc. C. 1970, 2441.
7. 7 with carbon monoxide that produced indoles, 3,4-dihydroquinazolin-4-ones, or 1,4-dihydro-2H-3,1- benzoxazin-2-ones.
8. Nishiyama, Y.; Maema, R.; Ohno, K.; Hirose, H.; Sonoda, N. Tetrahedron Lett. 1999, 40, 5717.
9. Nishiyama, Y.; Hirose, H.; Kitagaito, W.; Sonoda, N. Tetrahedron Lett. 2002, 43, 1855.
10. Nishiyama, Y.; Naitoh, Y.; Sonoda, N. Synlett 2004, 886.
11. 3 as eluent) to give the 2-aryl-1H-benzimidazoles.
12. Kondo, K.; Yokoyama, S.; Miyoshi, N.; Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1979, 18, 691.
13. For the transition-metal-catalyzed N-heterocyclization, it was suggested that the generation of the nitrene (or nitrenoid) intermediate was the key step in the reaction. For a review, see: Soderberg, B. C. G. Curr. Org. Chem. 2000, 4, 727.