Hassan Entesar A, Zayed Salem E, Mahdy Al-Hassan S, Abo-Bakr Ahmed M
Chemistry Department, Faculty of Science, South Valley University, Qena, 83523, Egypt.
Curr Org Synth. 2022;19(4):558-568. doi: 10.2174/1570179419666220104125340.
A series of new pyrimidines and thiazoles containing camphor moiety were synthesized under both conventional and microwave irradiation techniques.
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.
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.
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, H NMR, C 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.
在传统和微波辐射技术下合成了一系列含樟脑部分的新型嘧啶和噻唑。
樟脑与氨基胍或硫代氨基脲缩合分别得到樟脑肼甲脒2和樟脑硫代腙3。3与氯乙腈回流得到樟脑噻唑-4-亚胺4。化合物2和4用作合成目标产物的前体。
2与亚苄基丙二腈、乙酰丙酮和乙酰乙酸乙酯等不同物质反应得到相应的樟脑嘧啶衍生物5a、b - 7，而化合物4与醛、异吲哚酮、茚三酮、乙酸酐、苯磺酰氯和对硝基苯甲酰氯等不同试剂回流分别得到樟脑噻唑衍生物8a - d - 13。
在相同化合物的合成过程中对传统和环保型微波辐射方法进行了比较，结果表明后者更有效。元素分析、傅里叶变换红外光谱、氢核磁共振谱、碳核磁共振谱和质谱证实了所得新化合物的结构。对一些选定衍生物作为抗菌剂的潜在用途进行了研究并取得了有希望的结果。
