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Conventional and Microwave-Activated the Synthesis of a Novel Series of Imidazoles, Pyrimidines, and Thiazoles Candidates
Selim, Yasser,Abd El-Azim, Mohamed H.?M.
, p. 1403 - 1409 (2018)
A novel series of imidazoles, pyrimidines, and thiazoles were synthesized using microwave irradiation and conventional method from commercial available p-aminobenzoic acid. Thus, one-pot condensation of p-aminobenzoic acid, urea, and chloroacetic acid have been provided two types of imidazole derivatives as separated mixture 2a and 2b. [3?+?2?+?1] Cyclocondensation of 2a, benzaldehyde, and urea/thiourea in acidic medium afforded imidazolo oxazine derivative 3 and Imidazolothiazine 4. Coupling of 2a with benzene diazonium salt gave the phenyldiazenyl imidazolidine 5. While the reaction of 2a, thiourea, and benzaldehyde in sodium ethoxide afforded imidazolothiazine 6. Oxidative cyclization of thiourea derivative 7 resulted a mixture of benzithiazole derivative 7a and oxathiazole derivative 7b. Cyclocondensation of 7a with phenylenediamine and 4-methyl phenylenediamine furnished imidazole 8 and 9, respectively. Reaction of P-aminobenzioc acid with potassium cyanate followed by Biginelli reaction with (acetyl acetone, ethyl acetoacetate, and diethyl malonate) and salicyladehyde in HCl tolerated pyrimidine derivatives 10a–c, respectively. In the same manner, the reactions and short reaction time make microwave technique one of the greenest methodology for synthesis of this class of heterocyclic system.
