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صفحه اصلی
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بیست و نهمین کنفرانس شیمی آلی ایران
Application of Oxone/hydrogen peroxide (Oxone/H2O2) in the synthesis of nitrogen-containing heterocycles from alcohols
نویسندگان :
Zahra Mohammadi ( دانشگاه دامغان ) , Abolghasem Aghapour ( دانشگاه دامغان )
کلید واژه ها :
Benzimidazole،Quinoxaline،Oxone
چکیده مقاله :
Benzimidazoles and quinoxalines are considered as very important heterocyclic groups especially in pharmaceutical chemistry due to their very desirable properties such as anticancer, anti-inflammatory, antihypertensive, antiviral, antifungal, antibacterial, antioxidant and so on [1]. Very drugs and biological active compounds contain these structural scaffolds in their structures such as mebendazole as antiparasite, lansoprazole as antiulcer, and levomycin as antibiotic [2]. Here in the present work, an oxidative and one-pot method is described for the efficient conversion of alcohols and o-phenylenediamine to these valuable nitrogen containing heterocycles using Oxone/H2O2 as an oxidant system in the presence of potassium cyanide (Scheme 1). Different benzylic alcohols containing electron donating or withdrawing groups on aromatic ring can be converted to their corresponding benzimidazoles and also quinoxalines in good to excellent yields by this method. It was found that selective conversion of alcohols to desired benzimidazoles or quinoxalines is possible with controlling of reaction conditions such as solvent, the molar ratio of o-phenylenediamine to alcohol, and also reaction temperature. In addition, some other functional groups easily tolerate this chemoselective procedure so that they remain intact. The present work is important in terms of green chemistry due to its one-pot nature so that there is no need to separate aldehyde as intermediate product
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