An Efficient Protocol for the Synthesis of new Camphor Pyrimidine and Camphor Thiazole Derivatives using Conventional and Microwave Irradiation Techniques and In vitro Evaluation as Potential Antimicrobial Agents.

BACKGROUND

A series of new pyrimidines and thiazoles containing camphor moiety were synthesized under both conventional and microwave irradiation techniques.

METHODS

The condensation of camphor either with aminoguanidine or thiosemicarbazide gives the camphor hydrazine carboximidiamide 2 and the camphor thiosemicarbazone 3, respectively. Refluxing of 3 with chloroacetonitrile afforded the camphor thiazol-4-imine 4. Compounds 2 and 4 were used as precursors for the synthesis of target products.

RESULTS

The reaction of 2 with different species such as arylidene malononitrile, acetylacetone, and ethyl acetoacetate gave the corresponding camphor pyrimidine derivatives 5a,b-7 while refluxing of compound 4 with different reagents e.g. aldehydes, isatin, ninhydrin, acetic anhydride, benzene sulphonyl chloride, and p-nitro-benzoyl chloride afforded the camphor thiazole derivatives 8a-d- 13, respectively.

CONCLUSION

A comparison between the conventional and the eco-friendly microwave irradiation methods occurred during the synthesis of the same compounds, and the latter proved to be more efficient. The elemental analysis, FT-IR, 1H NMR, 13C NMR, and Mass spectra confirm the structures of the obtained new compounds. The potential use of some selected derivatives as antimicrobial agents was investigated and gave promising results.