Synthesis of some heterocyclic compounds derived from 2-mercapto pyrimidine

Abstract EN

In this work 2-hydrazino pyrimidine (1) was prepared from 2-mercapto pyrimidine with hydrazine hydrate.

Treatment of (1) with active methylene compounds gave 2-(3, 5-dimethyl -1 H – Pyrazole-1-yl) pyrimidine , whereas the reaction of (1) with carboxylic anhydride namely maleic anhydride or 1,2,3,6-tetra hydro ophthalmic anhydride yielded 1-Pyrimidine-2-yl-1, 2-dihydro pyridazine-3, 6-dione (3) and 2–Pyrimidine -2-yl -2, 3, 4 a, 5, 8 a–hexahedron phthalazine 1,4 – done (4).

Reaction of (1) with phenyl isothiocyanate and ethyl chloral acetate afforded 3-Phenyl-1, 3-thiazolidine-2,4-dione-2 pyrimidine -2- yl hydrazine (6) Azomethine (7-10) were prepared through condensation of (1) with aromatic aldehydes or ketones, and then compounds (7-9) are converted into a number of tetrazole derivatives (11-13).

Treatment of (1) with acetic acid afforded the derivative (14).

The reaction of 2-mercapto pyrimidine with ethyl chloral acetate afforded (15), whereas the reaction of (15) with thiosemicarbazide and 4 % sodum hydroxide leads to ring closure giving 1, 2, 4 triazole derivative (17).

Moreover the reaction of 2-mercapto pyrimidine with chore acetic acid gave (18) followed by refluxing (18) with o- amino aniline to give the Benz imidazole derivative (19).the structure of these compounds were characterized by FR-IR, UV spectra and some of them were characterized by element analysis.