Cu(I)‐Catalyzed Efficient Synthesis of 2′‐Triazolo‐nucleoside Conjugates

Abstract

A small library of thirty-two 2′-triazolyl uridine and 2′-triazolyl-5-methyluridine has been synthesized by Cu(I)-catalyzed condensation of 2′-azido-2′-deoxyuridine and 2′-azido-2′-deoxy-5-methyluridine with different alkynes and aryl propargyl ethers in almost quantitative yields. Triazolo-nucleoside conjugates, which can be evaluated for different biological activity for suitable drug development, were unambiguously identified on the basis of 1 H NMR, 13 C NMR, IR, and HRMS data analysis. These compounds have been synthesized for the first time and have not been reported in the literature earlier.

Click chemistry inspired syntheses of new amide linked 1,2,3-triazoles from naphthols: biological evaluation and in silico computational study

“…The 1,4-disubstituted-1,2,3-triazole derivatives 6a-m and 7a-m have been obtained by the 1,3-dipolar cycloaddition of 1-(prop-2-yn-1-yloxy)naphthalene 2a or 2-(prop-2-yn-1-yloxy)naphthalene 2b and 2-azido-N-phenylacetamides 5a-m via click chemistry approach (Scheme 1). The commercially available α-naphthol and β-naphthol were alkylated separately with propargyl bromide in the presence of K 2 CO 3 as a base in N,N-dimethylformamide (DMF) afforded the corresponding alkyne based naphthalene derivatives 2a and 2b respectively in 83-93% yields (Scheme 1) [47,48]. The synthesis of 2-azido-N-phenylacetamides 5a-m have been achieved from the corresponding anilines 3am via chloroacetylation using chloroacetyl chloride, followed by nucleophilic substitution with sodium azide in excellent yields (Scheme 1) [21,40] .…”

Synthesis of New 7,8-Dioxa[6]helicenes with Triazole Rings as Potential Molecular Tweezers

“…To synthesize compounds 7 and 8, first, a reaction of glyoxal bisulfite and malonaldehyde dimethylacetal with 2,7-dihydroxynaphthalene, respectively, was performed in acidic medium to obtain compounds 5 and 6. 9 Then, the products were etherified with propargyl bromide 10 followed by azide-alkyne cycloaddition reactions by using copper(I) bromide-N,N,N',N'',N''-pentamethyldiethylenetriamine (PMDETA) as a catalyst in DMF 11 (Scheme 1). Given that the nature of the substituents on the triazole ring affects the behavior of the ligand and their coordinating ability, 12 benzyl azide was preferred for the cycloaddition reaction in order to increase the coordination of triazole rings electronically.…”