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Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate

1
Engineering Laboratory of Organometallic, Molecular Materials and Environment (LIMOME), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, Fez 30000, Morocco
2
Laboratory of Scientific Research and Pedagogic Development (LSRPD) CRMEF Fez-Meknes, Meknes 50000, Morocco
3
Team of Organic Chemistry and Valorization of Natural Substances (COVSN), Faculty of Sciences, Ibn Zohr University, Agadir 80060, Morocco
4
Laboratory of Chemistry of Materials and Biotechnology of Natural Products, Faculty of Sciences, Moulay Ismail University, BP 11201, Meknes 50050, Morocco
*
Author to whom correspondence should be addressed.
Molbank 2020, 2020(4), M1167; https://doi.org/10.3390/M1167
Received: 5 November 2020 / Revised: 17 November 2020 / Accepted: 18 November 2020 / Published: 20 November 2020
(This article belongs to the Collection Molecules from Catalytic Processes)
The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis. View Full-Text
Keywords: triazole; α-amino phosphonic ester; click chemistry; carbazole; 2D-NMR spectroscopy triazole; α-amino phosphonic ester; click chemistry; carbazole; 2D-NMR spectroscopy
MDPI and ACS Style

Khadir Fall, S.A.; Achamlale, S.; Aouine, Y.; Nakkabi, A.; Faraj, H.; Alami, A. Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate. Molbank 2020, 2020, M1167.

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