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صفحه اصلی
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بیست و نهمین کنفرانس شیمی آلی ایران
Phosphoramidate synthesis via copper-catalysed oxidative coupling of amines and H-phosphonates
نویسندگان :
Zahra Abdi ( دانشگاه صنعتی خواجه نصیرالدین طوسی )
کلید واژه ها :
Phosphoramidate،Atherton-Todd reaction،H-phosphonate،Dialkyl phosphite
چکیده مقاله :
P-N bond creation is one of the great important research area owing to their myriad applications in organic synthesis. Between the various organophosphorous, including P(O)-N structural moiety, phosphoramidates are more efficient compounds in biologically active molecules, medicinal chemistry and industrial important products. For example, Sofosbuvir is an antiviral medicine that is used to treat chronic hepatitis C [1]. Traditional method of P(O)-N bond formation mainly relies on coupling of amines as a nucleophile with H-phosphinates. The Atherton-Todd reaction which generates phosphoryl chloride intermediate by halogenation of P(O)-H compounds with toxic halogenating agent such as CCl4, followed by the attack of nucleophile to phosphoryl chloride, give desire product. It is noticeable that traditional methods are inclined to suffer from low yields, react with restricted amines and the major drawbacks of the method include the use of toxic halogen sources. In this research, it has been tried to provide a more efficient method [2]. In the present study, we used CuI as the catalyst and Di-tert-butyl peroxide (DTBP) as the oxidant to obtain the phosphoramidate synthesis via copper-catalyzed oxidative coupling of amines and H-phosphonates. The purpose of this work is to synthesis of phosphoramidates with various amines in short time and highly yield products. (Scheme1).
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