Abstract
We have previously published new biheterocyclic phospohonic α-amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to the same catalytic process used previously, the compound naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate was synthesized with an excellent yield and high regioselectivity via the copper (I)-catalyzed alkyne–azide cycloaddition reaction (CuAAC), using diethyl (α-azido(benzamido)methyl)phosphonate (1) as a dipole and 2- naphthyl propiolate as a dipolarophile (2). The structure of the new compound was fully characterized by 1D (31P, 1H-, 13C-) and 2D (1H-1H and 1H-, 13C-) NMR spectroscopy, IR, and HRMS.
Highlights
Since they were first described in the literature in 1943 by the synthesis of aminomethane phosphonic acid, the study and synthesis of aminophosphonates and their derivatives have continued to proliferate [1]
In the perspective of improving our research work by finding new active formulas, we present in this paper the synthesis of a new triazolic α-aminophosphonate derivative, using the 1,3-dipolar cycloaddition by the “click chemistry” route
We opted for the Huisgen 1,3-dipolar cycloaddition reaction, catalyzed by copper (I) formed in situ by reduction of the Cu(II) salts (CuSO4, 5H2 O)
Summary
Since they were first described in the literature in 1943 by the synthesis of aminomethane phosphonic acid, the study and synthesis of aminophosphonates and their derivatives have continued to proliferate [1]. With these physicochemical properties related to their carboxylic analogs [2], they are known as peptide enzyme inhibitors due to their ability to mimic the transition states of amines and esters in biological processes [3]. Interesting applications of aminophosphonates have been discovered in several areas of life, ranging from medicine to agrochemistry [5,6,7] Their coupling with heterocyclic rings has opened up very interesting avenues in the search for new drugs against cancers [8]. It is no longer necessary to discuss their antimicrobial [10], antioxidant [11,12], and antiviral [13] characteristics
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