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Growing Science » Current Chemistry Letters » Preparation of N-heterylarenes from the perspective of phenylhydrazine-based under the principles green chemistry

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Current Chemistry Letters
ISSN 1927-730x (Online) - ISSN 1927-7296 (Print)
Quarterly Publication
Volume 13 Issue 4 pp. 753-760, 2024

Preparation of N-heterylarenes from the perspective of phenylhydrazine-based under the principles green chemistry Pages 753-760 Right click to download the paper Download PDF

Authors: Guillermo Penieres-Carrillo, Ricardo Alfredo Luna-Mora, Francisco Barrera-Téllez, Alejandro Martínez-Záldivar, Alicia Hernández-Campos, Rafael Castillo-Bocanegra, Ana M. R. C. Sousa, Hulme Ríos-Guerra

📋 Author Affiliations:
G. Penieres-Carrillo1, R.A. Luna-Mora1, F. Barrera-Téllez2, A. Martínez-Záldivar1, A. Hernández-Campos2, R. Castillo-Bocanegra2, A.M.R.C. Sousa3, H. Ríos-Guerra1
1 Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Av. 1 de mayo S/N, Estado de México, Cuautitlán Izcalli, CP 54740, Mexico
2 Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad de México, CP 04510, Mexico
3 Centro de Química, Universidade do Minho, Campus de Gualtar, Braga, 4710-057, Portugal
doi 10.5267/j.ccl.2024.3.006
Crossref 1 Source: CrossRef

🔑 Keywords: α-Nucleophile, Green chemistry, Hyperconjugation effect, Exo-dig closure reaction, H-bonding effects

Abstract: Herein, modern green synthesis approaches are studied to assemble N-heterylarenes scaffolds via a non-catalyzed intramolecular 5/6-exo-dig cyclocondensation reaction based on the in-situ generation of arenehydrazonopentan-/hexan-2-one. Accordingly, the formation of two N-heteryl moieties, pyrazol-1-yl and pyridazin-1(4H)-yl, was initially studied. Therefore, appropriate fluorophenyl was first converted into their respective phenylhydrazine by SNAr reaction and then reacted with different trigonal carbonyl bielectrophiles (-CO-, -CO2R, and -CO2H) in ethanol in the presence of US, MW, IR, and an IR· US irradiation mixture. Cyclic nitrogenous cores were best obtained when subjected to microwave irradiation with ketone and arylhydrazine as starting reagents, allowing them to get excellent yields quickly. Arylhydrazine reactants featuring Π-donor groups underwent the best 5/6-exo-dig type annulment reaction. Presumably, the observed improvements in EDG-dependent reaction efficiency reflect changes in the nucleophilicity of arylhydrazines intermediates as α-nucleophilic reactants.

How to cite this paper
APA: Penieres-Carrillo, G., Luna-Mora, R., Barrera-Téllez, F., Martínez-Záldivar, A., Hernández-Campos, A., Castillo-Bocanegra, R., Sousa, A & Ríos-Guerra, H. (2024). Preparation of N-heterylarenes from the perspective of phenylhydrazine-based under the principles green chemistry. Current Chemistry Letters, 13(4), 753-760.
Chicago/Turabian: Penieres-Carrillo, G., Luna-Mora, R., Barrera-Téllez, F., Martínez-Záldivar, A., Hernández-Campos, A., Castillo-Bocanegra, R., Sousa, A & Ríos-Guerra, H. 2024. "Preparation of N-heterylarenes from the perspective of phenylhydrazine-based under the principles green chemistry." Current Chemistry Letters 13, no. 4 (2024): 753-760.
AMA: Penieres-Carrillo, G., Luna-Mora, R., Barrera-Téllez, F., Martínez-Záldivar, A., Hernández-Campos, A., Castillo-Bocanegra, R., Sousa, A & Ríos-Guerra, H. Preparation of N-heterylarenes from the perspective of phenylhydrazine-based under the principles green chemistry. Current Chemistry Letters. 2024;13(4):753-760.

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📚 Journal: Current Chemistry Letters | 📅 Year: 2024 | 📖 Volume: 13 | 📄 Issue: 4 | 👁️ Views: 840 | 📊 Crossref: 1

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