In this study, we synthesize 2-amino-4-alkyl/aryl-6-(hydroxymethyl)-8-oxopyrano[3,2-b] pyran-3-carbonitriles derivatives using a multicomponent reaction featuring aromatic or aliphatic aldehydes, kojic acid, and malononitrile catalyzed by nano fluoroapatite doped with Si and Mg (Si–Mg–FA). All reactions were carried out in EtOH as the solvent under reflux and green condition. The process demonstrates various advantages, including high yields, short reaction times, and simple workup. In addition, toxic organic solvent is not used, nor is chromatographic purification of products required. We characterized the synthesized compounds by Fourier transform infrared, ¹³CNMR, and ¹HNMR spectroscopies. Additionally, the antibacterial properties of the pyrano[3,2-b]pyran derivatives were evaluated by determining the minimum inhibitory concentration on two gram-positive and gram-negative bacteria using the macro dilution method and compared with Penicillin and Tetracycline at the same conditions. The 2-amino-4-(2,4-dichlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile and the 2-amino-4-hexyl-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile show the best antibacterial activity with a MIC value of 62.5 μg/ml against Staphylococcus aureus (ATCC 25923). Moreover, the antioxidant properties of the pyrano[3,2-b] pyrans derivatives were evaluated. It is notable that pyrano[3,2-b] pyrans derivatives, synthesized with substituent groups on benzaldehyde such as-NO₂, -COOCH₃, -OMe show the best antioxidant activity measured by DPPH radical-scavenging method.

中文翻译：

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纳米Si–Mg–氟磷灰石催化剂绿色合成吡喃并[3,2-b]吡喃衍生物并评估其抗菌和抗氧化性能

在这项研究中，我们使用具有芳香族或脂肪族醛，曲酸的多组分反应合成了2-氨基-4-烷基/芳基-6-（羟甲基）-8-氧杂吡喃[3,2-b]吡喃-3-腈的衍生物，以及掺杂有Si和Mg（Si–Mg–FA）的纳米氟磷灰石催化的丙二腈。所有反应均在回流和绿色条件下在作为溶剂的EtOH中进行。该方法显示出各种优点，包括高产率，短反应时间和简单的后处理。此外，不使用有毒的有机溶剂，也不需要色谱纯化产品。我们通过红外傅立叶变换，¹³ CNMR和¹表征了合成的化合物HNMR光谱学。此外，吡喃并[3,2-b]吡喃衍生物的抗菌性能通过使用宏观稀释法确定两种革兰氏阳性和革兰氏阴性细菌的最小抑菌浓度来评估，并在相同条件下与青霉素和四环素进行比较。2-氨基-4-（2,4-二氯苯基）-4,8-​​二氢-6-（羟甲基）-8-氧代-吡喃并[3,2-b]吡喃-3-腈和2-氨基- 4-己基-4,8-​​二氢-6-（羟甲基）-8-氧代-吡喃并[3,2-b]吡喃-3-甲腈显示最佳的抗菌活性，其对金黄色葡萄球菌的MIC值为62.5μg/ ml（ATCC 25923）。此外，还评估了吡喃并[3,2-b]吡喃衍生物的抗氧化性能。值得注意的是，与苯甲醛上的取代基如-NO ₂，-COOCH ₃，-OMe合成的吡喃并[3,2-b]吡喃衍生物显示出通过DPPH自由基清除方法测得的最佳抗氧化活性。