Abstract
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 phthalic anhydride yielded 1-Pyrimidine-2-yl-1,2-dihydro pyridazine-3,6-dione (3) and 2 – Pyrimidin -2-yl -2,3,4 a ,5,8 a – hexahydro phthalazine 1,4 – dione (4) . Reaction of (1) with phenyl isothiocyanate and ethyl chloro acetate afforded 3-Phenyl-1,3-thiazolidine-2,4-dione-2( pyrimidine -2- yl hydrazone (6) Azomethine (7-10) were prepared through condensation of (1) with aromatic aldehydes or ketones, 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 chloro 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 chloro acetic acid gave (18) followed by refluxing (18) with o- amino aniline to give the benzimidazole derivative (19).the structure of these compounds were characterized by FR-IR, UV spectra and some of them were characterized by element analysis.
Highlights
We report on the synthesis of compounds derived from 2-mercapto pyrimidine containing pyrazole, Pyridazione thiazolidinone, tetrazole
(1) which was prepared by the reaction of 2-mercapto pyrimidine with hydrazine hydrate The Starting material for the synthesis of targeted compounds is 2-hydrazino pyrimidine
Treatment of Shiff's bases (7-9) with (NaN3) produced tetrazole derivatives(10-13). Structures of these compound, were confirmed by the disappearance of band at (1600-1640)cm-1, attributed to (C=N) stretching frequency which was agood evidence for the success of this step of reaction. Beside this, FTIR spectra of these compounds were devoid of a strong band at (2160-2120)cm-1 attributed to stretching frequency of azide group
Summary
Pyrazole derivatives have attracted particular interests during the last twenty five years due to the use of such ring system as the core structure in many drug substances , covering wide range of pharmacological applications [1,2]. Thiazolidinone derivatives play a vital role owing to their wide range of biological activity and industrial importance as stabilizers for polymeric materials [4,5]. Benzimidazole and its derivatives have attracted researcher's interest in the fields of bioorganic and medical chemistry to their significant antifungal, antibacterial and insecticidal properties [11]. We report on the synthesis of compounds derived from 2-mercapto pyrimidine containing pyrazole, Pyridazione thiazolidinone, tetrazole,. (1) which was prepared by the reaction of 2-mercapto pyrimidine with hydrazine hydrate The Starting material for the synthesis of targeted compounds is 2-hydrazino pyrimidine.
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