An efficient and easy method for the synthesis of 1-(coumarin-3-carbonyl)guaiazulene derivatives by the condensation of 1-cyanoacetylguaiazulene and 2-hydroxyaldehydes in the presence of ammonium acetate has been described. The structures of all target compounds have been confirmed by NMR, IR, MS spectra and elemental analysis, and the bioassay result indicated that some of the title compounds had relatively antibacterial activity.
A simple and efficient procedure for the preparation of 3,3'-aryl(alkyl)-bis(4-aminocoumarine)s has been developed by the reaction of 4-hydroxycoumarin and aldehydes in MeOH under room temperature conditions in the presences of KHSO 4 as a catalyst. 1,4-Dihydropyridino [3,2-c][5,6-c]dicoumarines were also obtained via condensation of 4-hydroxycoumarin and aldehydes in HOAc under reflux conditions in good yields. All of above compounds have been confirmed by IR, NMR spectra and elemental analysis. Keywords 4-aminocoumarine; aldehyde; 3,3'-aryl(alkyl)-bis(4-aminocoumarine); 1,4-dihydropyridino[3,2-c][5,6-c]dicoumarine; KHSO 4 ; synthesis 香豆素衍生物是一类广泛存在于自然界中的重要 杂环化合物, 具有明显的抗凝结、抗癌症及抗 HIV (Human Immunodeficiency Virus)等生物活性 [1] . 其中一 些 3-取代香豆素, 尤其是 3,3′-芳基二(香豆素)类化合物 表现出显著的抗 HIV 活性 [2] 、抗病毒活性 [3] 及脲酶抑制 活性 [4] . 另外, 吡啶并香豆素类化合物由于具有抑制单 胺氧化酶 [5] 、抗肿瘤 [6] 、止痛 [7] 等活性, 引起人们的关注. 随着人们对该类杂环化合物的深入研究和广泛应用, 发 现和筛选具有新颖化学结构和高效低毒药理活性的香 豆素类衍生物, 成为香豆素化学研究领域中的一个热 点.有关香豆素的 3-位烷基化及环化反应的研究, 以 4-羟基香豆素 [8] 为基本原料的研究很多, 如与醛或 α,β-不 饱和酮类化合物的烷基化 [9] , 与芳香醛和丙二睛的烷基 化、环化反应 [10] 等, 但是以 4-氨基香豆素为基础原料的 相关反应研究相比还比较少 [11] .
An efficient and easy method for the synthesis of coumarino [4,3-b]pyran-4-one derivatives underwent oxidative cyclization of 3-cinnamoyl-4-hydroxycoumarins, synthesized from condensation between 3-acetyl-4-hydroxycoumarin and aromatic aldehydes in the presence of piperidine and PEG-400 by using iodine in DMSO, has been described. All of above compounds have been confirmed by NMR, IR, MS spectra and elemental analysis.
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