Synthesis and antimicrobial activity of certain pyrimidine derivatives

Hydrazinolysis of 3 gave compounds 4, 5 and 6 according to reaction conditions. Certain fused pyrimidine derivatives such as triazolo compound [7] and tetrazolo [8] were obtained from the reaction of 4 with CS2/NaOH and NaNO2/HCL, respectively. Refluxing 4 with chloroacetyl chloride yielded compounds 13 and 15 according to reaction conditions. On the other h and, reacting 3, 5 and 6 with some aldehydes gave 9a-e, 17a-e and 22a-g. Treating 5 with acetyl acetyl acetone and isothiocyanates afforded compounds 18 and 19a, b, respectively. Condensation of 1, 4, 5 and 6 with p-toluene sulfonyl chloride furnished 11, 12, 16 and 21, respectively. The benzyl derivative [23] was converted into the chloroderivative [24] which was reacted with some amines to yield 25. Also, compound 26 was obtained from 23. Some of the synthesized compounds were screened for their antimicrobial activity

Stereochemistry of alpha-cyanation of 4-acetamido-1-methylpiperidine

Alpha-cyanation of 4-acetamido-1-methylpiperidine [1] was carried out by reacting the corresponding N-oxide 2 with p-toluenesulphonyl chloride followed by the addition of KCN. 1H-NMR analysis of the produced aminonitrile indicated that the addition of cyanide ion to the iminium intermediate 5, that has been generated in the reaction, occurred in stereospecific manner to afford the transdiastereomer 6b