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Synthesis and Antimicrobial Activity of Some New Coumarin and Dicoumarol Derivatives
Russian Journal of Bioorganic Chemistry ( IF 1.1 ) Pub Date : 2020-05-01 , DOI: 10.1134/s1068162020030176
M. K. A. Regal , S. S. Shaban , S. A. El-Metwally

Abstract Phase transfer catalysis reaction of 4-hydroxy-6-methyl-2 H -chromen-2-one with alkyl halides afforded C 4 oxygen alkylation products of 2 H -chromen-2-one derivatives in appreciative yield, whereas with phenyl isothiocyanate gives the C 3 addition product of 4-hydroxy-6-methyl-2-oxo- N -phenyl-2 H -chromene-3-carbothioamide, also one pot three component phase transfer reaction was investigated. Treatment of 4-hydroxy-6-methyl-2 H -chromen-2-one with aromatic aldehydes in different molar ratios gives 3‑arylidine and the dicoumarol derivatives . However pyrano chromene and pyrano pyridine were obtained by reaction of arylidine with ethyl acetoacetate through Michael cycloaddition reaction. The stability of pyrone ring in 3-arylidine and dicoumarol towards different nucleophilic reagents under reflux and/or fusion conditions has been studied by the action of, hydrazine hydrate, ammonium acetate, methyl amine and p -toluidine afforded compounds 1,2-bis(benzo[ d ][1,3]dioxol-5-ylmethylene)hydrazine, 1,2-bis(4-methoxybenzylidene)hydrazine and 2,6-bis((2,6-dihydroxy-3-methylphenyl)(hydroxy)methylene)-1-(4-methoxyphenyl)-4-( p -tolyl) piperidine-3,5-dione derivatives. The antimicrobial activity of some synthesized compounds has been investigated.

中文翻译:

一些新型香豆素和双香豆素衍生物的合成及抗菌活性

摘要 4-羟基-6-甲基-2 H-chromen-2-one 与卤代烷的相转移催化反应以可观的收率提供了 2 H-chromen-2-one 衍生物的 C 4 氧烷基化产物,而异硫氰酸苯酯则得到研究了4-羟基-6-甲基-2-氧代-N-苯基-2H-色烯-3-碳硫酰胺的C 3 加成产物,以及一锅三组分相转移反应。用不同摩尔比的芳香醛处理 4-hydroxy-6-methyl-2 H-chromen-2-one 得到 3-芳基烷和双香豆素衍生物。然而,吡喃并色烯和吡并吡啶是通过芳烷与乙酰乙酸乙酯通过迈克尔环加成反应得到的。通过水合肼、醋酸铵、甲胺和对甲苯胺的作用,研究了在回流和/或融合条件下,3-芳基和双香豆素中吡喃酮环对不同亲核试剂的稳定性,得到化合物1,2-双(苯并[d][1,3]二氧戊环-5-基亚甲基)肼、1,2-双(4-甲氧基亚苄基)肼和2,6-双((2,6-二羟基-3-甲基苯基)(羟基)亚甲基)-1-(4-甲氧基苯基)-4-(对甲苯基)哌啶-3,5-二酮衍生物。已经研究了一些合成化合物的抗微生物活性。6-二羟基-3-甲基苯基)(羟基)亚甲基)-1-(4-甲氧基苯基)-4-(对甲苯基)哌啶-3,5-二酮衍生物。已经研究了一些合成化合物的抗微生物活性。6-二羟基-3-甲基苯基)(羟基)亚甲基)-1-(4-甲氧基苯基)-4-(对甲苯基)哌啶-3,5-二酮衍生物。已经研究了一些合成化合物的抗微生物活性。
更新日期:2020-05-01
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