Benzyl methyl morpholinium ascorbate [BMMorph][Ascorb] as an efficient catalyst and media for ‘Click’ synthesis of 1,2,3-triazolyl based carboacyclic nucleoside

سال انتشار: 1397
محل انتشار: بیستمین کنگره شیمی ایران
کد COI اختصاصی: IRANCC20_404
زبان مقاله: انگلیسی
تعداد مشاهده: 419

نویسندگان

Medicinal Chemistry Research Laboratory, Department of Chemistry, Shiraz University of Technology,Shiraz ۷۱۵۵۵-۳۱۳, Iran

چکیده

1,2,3-Triazoles are an important class of heterocyclic compounds, that interest in their synthesis stems from their wide range of applications in pharmaceuticals, agrochemicals, dyes, photographic materials, corrosion inhibition, etc. and biological activities such as antiviral, antiepileptic, antiallergic, anticancer, anti-HIV,antimicrobial activities against gram positive bacteria and β3-adrenergic receptor agonist. Due to such multifarious applications different methods have been exploited for their synthesis and amongst them Huisgen 1,3-dipolar cycloaddition of azides with alkynes is the most popular method for the construction of 1,2,3-triazole framework. The incorporation of 1H-1,2,3-triazolyl group into a molecular scaffold is an interesting task, since the 1H-1,2,3-triazolyl moiety involves remarkable biological activities, as well as recognition by enzymes and receptors in the cell . Moreover, 1H- 1,2,3- triazolyl cores are known as the non-classical isostere of amide because of having considerable topological and electronic similarities. Given the biological importance of 1H-1,2,3-triazolyl cores, they have been extensively used in the design of new nucleosides as surrogate moieties in different fragments of the nucleosides. Hereby, we have described the synthesis of benzyl methyl morpholinium ascorbate [BMMorph][Ascorb] and its application in ‘Click’ synthesis of 1,2,3-triazolyl based carboacyclic nucleoside (1) in good to excellent yields (Scheme 1). In this reaction, [BMMorph][Ascorb] was used to catalyze the cycloaddition reaction of some Npropargyl nucleobases or heterocyclic compounds with β-azidoalcohols in the presence of CuSO4.5H2O in aqueous media at reflux condition [1].

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