Chemoselective Reactions of Amidines:  Selective Formation of Iminopyrimidine Regioisomers

Autor: McCauley, J. A., Theberge, C. R., Liverton, N. J.
Zdroj: Organic Letters; October 2000, Vol. 2 Issue: 21 p3389-3391, 3p
Abstrakt: The dramatic effect of base on the chemoselectivity of the reaction of amidines with substituted 3-phenyl-2-propynylnitriles is demonstrated. Amidine 1 can be added to cyanoalkyne 2 to give iminopyrimidine isomer 3 with high selectivity. The addition of 2 equiv of NaHMDS completely reverses the selectivity of the reaction, yielding isomer 4 almost exclusively. This method has been used to prepare a variety of substituted 4-iminopyrimidines.
Databáze: Supplemental Index