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

Khadir Fall, Serigne Abdou; Achamlale, Saïd; Aouine, Younas; Nakkabi, Asmae; Faraj, Hassane; Alami, Anouar

doi:10.3390/M1167

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

by

Serigne Abdou Khadir Fall

¹,

Saïd Achamlale

^1,2

,

Younas Aouine

^1,3

,

Asmae Nakkabi

⁴,

Hassane Faraj

¹ and

Anouar Alami

^1,*

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

Submission 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)

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Abstract

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.

Keywords: triazole; α-amino phosphonic ester; click chemistry; carbazole; 2D-NMR spectroscopy

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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. https://doi.org/10.3390/M1167

AMA Style

Khadir Fall SA, 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(4):M1167. https://doi.org/10.3390/M1167

Chicago/Turabian Style

Khadir Fall, Serigne Abdou, Saïd Achamlale, Younas Aouine, Asmae Nakkabi, Hassane Faraj, and Anouar Alami. 2020. "Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate" Molbank 2020, no. 4: M1167. https://doi.org/10.3390/M1167

APA Style

Khadir Fall, S. A., Achamlale, S., Aouine, Y., Nakkabi, A., Faraj, H., & Alami, A. (2020). Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate. Molbank, 2020(4), M1167. https://doi.org/10.3390/M1167

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

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