Chemistry of Natural Compounds ( IF 0.8 ) Pub Date : 2024-01-31 , DOI: 10.1007/s10600-024-04267-w S. V. Cojocari , S. N. Curlat , F. Z. Macaev
New 1,3-disubstituted 2,2-dimethylcyclopropanes of the isoxazole and pyrazole series were synthesized starting from (+)-3-carene. Olefination of the reductive ozonolysis product of (+)-4-acetyl-2-carene produced 1R-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane, further reaction of which with hydroxylamine or hydrazines led to heterocyclic compounds. It was shown that 3,5-dimethylpyrazoles could be synthesized on the surface of Al2O3 using ultrasonic irradiation. Studies of the antimicrobial activity of heterocyclic derivatives of dibromovinyl-2,2-dimethylcyclopropane found significant fungicidal effects of pyrazoles 8, 10, and 11 with weak antibacterial activity.
中文翻译:
基于(+)-3-蒈烯的异恶唑和吡唑系列1R-顺-二溴乙烯基-2,2-二甲基环丙烷的合成
以(+)-3-蒈烯为原料,合成了异恶唑和吡唑系列的新型1,3-二取代2,2-二甲基环丙烷。 (+)-4-乙酰基-2-蒈烯的还原性臭氧解产物烯化生成1R-顺式-3-(2,2-二溴乙烯基)-2,2-二甲基环丙烷,其进一步与羟胺或肼反应得到杂环化合物。结果表明,超声波照射可以在Al 2 O 3表面合成3,5-二甲基吡唑。对二溴乙烯基-2,2-二甲基环丙烷杂环衍生物的抗菌活性研究发现,吡唑类8、10、11具有显着的杀菌作用,但抗菌活性较弱。