Objective: To develop efficient method for the synthesis of naphtha-quinoxaline derivatives via the reaction of β-lapachone with various 1,2-diamines.

Methods: A mixture of β-lapachone (1mmol), 1,2-diamine (1mmol) and graphene oxide (20mg) in methanol (3mL) was heated at 60°C, under constant stirring for appropriate time. After completion of the reaction, the catalyst was filtered off, washed with ethyl acetate (3x3mL) and the combined filtrate was washed with H2O, dried (anhy. Na2SO4) and concentrated under vacuum. The residue was chromatographed over a column of silica gel eluting with a mixture of hexane and ethyl acetate in different ratios, to afford the desired product. All synthesized compounds were assigned with the help of analytical and 1H, 13C NMR, IR, and mass spectral studies.

Results: To establish the catalytic role of GO in the synthesis of naphtha-quinoxaline derivatives, the reaction of β-lapachone with 3,4-diaminotoluene was selected as a model reaction. The catalytic activity of graphene oxide in comparison with other catalysts like acidic resin amberlyst-15 and solid acid catalyst like montmorillonite K-10 were studied. The reaction was also observed in various solvents such as water, acetonitrile, toluene, dichloromethane, ethanol and 1,4-dioxane using GO as a catalyst. Excellent yields were obtained at 60°C in methanol. The efficacy of the present protocol was investigated by the reaction of β- lapachone with other 1,2-diamines.

Conclusion: An attractive green metal free carbocatalyst Graphene Oxide (GO) has been successfully utilized for the expedient synthesis of naphtha-quinoxaline derivatives. GO showed high catalytic activity which is attested by the desired products being produced in shorter time. The main advantage of this method is the reusability of the catalyst which makes the procedure sustainable.

目的：建立一种通过β-拉帕酮与各种1,2-二胺反应合成石脑油-喹喔啉衍生物的有效方法。

方法：将β-拉帕酮（1mmol），1,2-二胺（1mmol）和氧化石墨烯（20mg）在甲醇（3mL）中的混合物在恒定搅拌下于60°C加热适当的时间。反应完成后，将催化剂滤出，用乙酸乙酯（3×3mL）洗涤，并将合并的滤液用H 2 O洗涤，干燥（无水Na 2 SO 4）并在真空下浓缩。将残余物在硅胶柱上进行色谱分离，用不同比例的己烷和乙酸乙酯的混合物洗脱，得到所需产物。在分析和1H，13C NMR，IR和质谱研究的帮助下，对所有合成的化合物进行了分配。

结果：为了建立GO在石脑油-喹喔啉衍生物合成中的催化作用，选择了β-拉帕酮与3,4-二氨基甲苯的反应作为模型反应。与其他催化剂（如酸性树脂amberlyst-15）和固体酸催化剂（如蒙脱土K-10）相比，研究了氧化石墨烯的催化活性。还使用GO作为催化剂在各种溶剂如水，乙腈，甲苯，二氯甲烷，乙醇和1,4-二恶烷中观察到该反应。在60℃下在甲醇中获得优异的产率。通过β-拉帕酮与其他1,2-二胺的反应研究了本方案的功效。

结论：有吸引力的绿色环保无碳催化剂氧化石墨烯（GO）已成功用于合成石脑油-喹喔啉衍生物。GO表现出较高的催化活性，这可通过在更短的时间内生产所需的产品来证明。该方法的主要优点是催化剂的可重复使用性，使该过程可持续。