3-cyanoacetylindole as a building block in the synthesis of nonfused and fused pyridine, pyrimidine, diazepine and pyranone derivatives

ABSTRACT

The reaction of 3-cyanoacctylindole I with trichloroacetonitrile afforded trichloroll1cthylpropen-1-one derivative 3 which upon the reaction with an excess of trichloroacetonitrilc yielded the ditrichlorome-thylpyrimidine derivative 5. It was converted to a variety of pyrazolo 7, dihydrazino 9. and isoxazolo pyrimidine II derivatives. The enaminonitrile 2 was used as a substrate to form the pyridine 13, 14, 16, diazepine 20 and pyranone 22 as well as 1, 2, 4-triazolo-25. 1, 2, 3, 4-tetrazolo-27, and benzimidazolo-pyrimidine 29 derivatives