Novel synthesis, ring transformation and anticancer activity of 1,3-thiazine, pyrimidine and triazolo[1,5-a]pyrimidine derivatives

Bulletin of The Chemical Society of Ethiopia

H. A. El-Sayed¹ 

关键词: 1;    3-Thiazine;    Pyrimidine;    Triazole;    Pyrazole;    Anticancer activity;   

DOI  :  10.4314/bcse.v32i3.10

学科分类：化学（综合）

来源: Chemical Society of Ethiopia

【 摘 要 】

Synthesis, heterocyclization and anticancer activity of a new series of heterocyclic compounds are described. Aminothiazine 1 was obtained from the base induced condensation of thiourea, benzaldehyde and ethyl cyanoacetate. The synthesis of N -phenyl amino pyrimidine derivative 2 was obtained as a result of reaction of aniline with compound 1 . Compound 2 underwent ring opening and recyclization upon reaction with HCl or H₂O₂/ NaOH to afford the acid derivative 3 or oxazine 4 , respectively. Thiazine 1 undergoes ring transformation upon the effect of NH₂OH.HCl to produce pyrimidine derivative 5 . Heterocyclization of compound 1 with thiosemicarbazide followed by oxidation with I₂/AcOH afforded triazolopyrimidine 6 and 7, respectively. Alkylation of compound 1 was promoted by reaction of 1 with ethyl iodide to give alkylated thiazine 8 which in turn undergo ring transformation when subjected to reaction with hydrazine hydrate to give pyrazole derivative 9 . Refluxing of amino-1,3-thiazine derivative 1 with ethyl bromoacetate in the presence of Et₃N produce the alkylated pyrimidine product 10 . Hydrazonolysis of 1,3-thiazine 1 with hydrazine or phenyhydrazine gave pyrimidine derivatives 11a,b , respectively. Compound 11b was cyclized with carbon disulfide or formaldehyde to produce triazolopyrimidines 12 and 13 , respectively. Some of the new compounds were screened for anticancer activity and significant results were found for some compounds.

【 授权许可】

Unknown