Selective synthesis of 2-, 4-, and 5-cyano substituted imidazoles from imidazole N-oxides and trimethylsilyl cyanide

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6971-6973

  Alcázar, Jesús ^a   Begtrup, Mikael ^b   De La Hoz, Antonio ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343847545     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960991s     Document Type: Article

References (11)

1. Vorbrüggen, H.; Krolikiewicz, K. Synthesis 1983, 316.
2. Sakamoto, T.; Haneda, S.-I.; Nishimura, S.; Yamanaka, H. Chem. Pharm. Bull. 1985, 33, 565.
3. Vorbrüggen, H. Acc. Chem. Res. 1995, 28, 509.
4. Sato, N.; Shimomura, Y.; Ohwaki, Y.; Takeuchi, R. J. Chem. Soc., Perkin Trans. 1 1991, 2877.
5. Sakakibara, T.; Ohmaki, Y.; Sato, N. Bull. Chim. Soc. Jpn. 1993, 66, 1149.
6. Yamanaka, H.; Nishimura, S.; Kaneda, S.-I.; Sakamoto, T. Synthesis 1984, 681.
7. Alcázar, J.; Begtrup, M.; de la Hoz, A. J. Chem. Soc., Perkin Trans. 1 1995, 2467.
8. (a) Marcus, Y. J. Chem. Soc. Rev. 1993, 409.
9. (b) Reichardt, C. Chem. Rev. 1994, 94, 2319.
10. 4- and 5-Cyanoimidazoles can be transformed, by reduction to aminometilimidazoles, analogs of midazolam or nizofenone with anticonvulsant or tranquilizer properties. See for instance Bhattacharyya, P. K.; Grant, A. Anal. Chim. Acta. 1982, 142, 249.
11. Addition at the reaction temperature is crucial. If the addition was performed at 20°C followed by heating to the reaction temperature, the product distribution corresponded to that obtained by keeping the temperature at 20°C.