Naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate

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, accordi...

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Bibliographic Details
Published in:MolBank 2021-12, Vol.2021 (4), p.M1285
Main Authors: Fall, Serigne Abdou Khadir, Hajib, Sara, Karai, Oumaima, Boukhssas, Salaheddine, Aouine, Younas, Akhazzane, Mohamed, Labriti, Brahim, Faraj, Hassane, Alami, Anouar
Format: Article
Language:English
Subjects:
1,3-dipolar cycloaddition
1D and 2D NMR
Alkynes
By products
Cancer
Carbazoles
Chemistry
click chemistry
Cycloaddition
Dipoles
Esters
Ethanol
HRMS
Infrared spectroscopy
Mass spectrometry
NMR spectroscopy
Phosphonates
Phosphorus
Regioselectivity
Scientific imaging
triazole
Triazoles
α-amino phosphonic ester
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Summary: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.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1285