Abstract
1,2,4-Triazine and 1,2,5-oxadiazine derivatives 2–12 were obtained from treated 1,3-oxazolone (1) with phenyl hydrazine or hydroxylamine hydrochloride. Chlorotriazine derivative 3 undergoing condensation reactions with different reagents produced new fused tetrazolo-triazine and triazino-quinazolinone derivatives. 1,2,5-Oxadiazine has been used as a synthon for the fused pyrazolo-oxadiazine derivative. The constitution of the prepared compounds was built up based on microanalytical and spectral data. Some of the new compounds were assessed for their antimicrobial activity.
Highlights
Compound 2 could be present in lactam-lactim tautomers (2A and 2B), but the lactam form is thermodynamically more stable because the oxo form is more stabilized by 54.4 kJ mol− 1 than the enol form [17]. e structure of 2 can be deduced from its spectroscopic properties. e IR spectrum showed a band correlated with C O lactam at 1690 cm− 1
1HNMR spectrum showed one broad singlet signal in the down eld region correlated with the NH proton
Re uxing of compound 2 with phosphorus oxychloride and phosphorus pentachloride produces the chlorotriazine derivative 3 which is used as a synthon for new triazine derivatives (Scheme 1)
Summary
E structure of compound 4 established chemically by refluxing in acetic anhydride yielded the N,N′-diacetyl derivative 5 (Scheme 2).
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