Molbank (Oct 2021)

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

  • Serigne Abdou Khadir Fall,
  • Sara Hajib,
  • Oumaima Karai,
  • Salaheddine Boukhssas,
  • Younas Aouine,
  • Mohamed Akhazzane,
  • Brahim Labriti,
  • Hassane Faraj,
  • Anouar Alami

DOI
https://doi.org/10.3390/M1285
Journal volume & issue
Vol. 2021, no. 4
p. M1285

Abstract

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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.

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