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1
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85069412408
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This paper is dedicated to the memory of our colleagues Ken Tubman and Lendon Pridgen, deceased August 1, 1999
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This paper is dedicated to the memory of our colleagues Ken Tubman and Lendon Pridgen, deceased August 1, 1999.
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2
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For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
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For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
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3 in MeOH). However, fairly subtle stereoelectronic effects seem to govern the outcome of these reactions. For example, C,N-diaryl- and C,N-dialykylimines react with TosMIC to give the corresponding imidazoles in good to excellent yields while C-aryl,N-alkylimines react poorly with TosMIC to give low yields of imidazole product (0-37%). In the only example of its kind reported, the methyl-substituted TosMIC reagent combines with a C,N-diarylimine to give the imidazole in 75% yield, but required the action of NaH in an aprotic solvent (DME).
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