Assessment of amination reactions via nucleophilic aromatic substitution using conventional and eco-friendly energies

ABSTRACT

The efficiency of conventional heating energy source compared with Infrared (IR), Ultrasound (US), Microwave and the simultaneous combination US–IR eco-friendly approaches for preparation of new N-(5-R¹ _-amino-2-nitrophenyl)acetamides and 5-R¹-amino-2-nitroaniline by Nucleophilic Aromatic Substitution (S_NAr) via addition–elimination reactions on the halogens F, Cl, Br, I, employing amines as nucleophiles were explored. Moreover, phenyldiazenyl derivatives in good yields by an oxidative one-pot S_NAr-based amination reaction from an unusual oxidation of 2-phenylhydrazinyl derivatives in DMSO was prepared.

GRAPHICAL ABSTRACT

KEYWORDS:

• S_NAr reactions
• amino(acetamido)-halo-nitro aromatic compounds
• assessment
• thermal energy
• alternative energy sources

Disclosure statement

No potential conflict of interest was reported by the authors.

Notes on contributors

Ricardo A. Luna-Mora is Ph.D. candidate in Organic Chemistry at National Autonomous University of Mexico (UNAM). His research interests lie in synthesis and reactivity of benzimidazoles and Green Chemistry.

Ángeles Torres-Reyes is student of the Degree in Chemistry at UNAM.

Oscar A. González-Cruz is Student of the Degree in Chemistry at UNAM.

Fernando Ortega-Jiménez is Ph.D. in Organometallic Chemistry. He is currently assistant professor in the Department of Chemistry in FES Cuautitlán-UNAM. His research interests lie in synthesis and catalyst of palladium complexes and Green Chemistry.

Hulme Ríos-Guerra is Ph.D. in Medicine Investigation. He is currently assistant professor in the Department of Chemistry in FES Cuautitlán-UNAM. His research interests lie in synthesis and application in medicine of heterocycles.

Jessica V. González-Carrillo is student of the Degree in Chemical Engineering at UNAM.

Francisco Barrera-Téllez is student of the M.S. Degree in Chemistry at UNAM.

Javier Perez-Flores is Ph.D. in Organic Chemistry. He is currently academic technician in the Department of Mass Spectrometry in Chemistry Institute – UNAM. His research interests lie in the study of mass spectrometry of organic compounds.

José G. Penieres-Carrillo is Ph.D. in Organic Chemistry. He is currently titular professor of university in the Department of Chemistry in FES Cuautitlán – UNAM. His research interests lie in Green Chemistry and synthesis and reactivity of heterocyclic compounds.

ORCID

José G. Penieres-Carrillo http://orcid.org/0000-0003-2085-7813

Additional information

Funding

The authors thank DGAPA-UNAM PAPIIT IN218515 and FES Cuautitlán-UNAM PIAPI1618 projects and also thank CONACYT for the grant 32841.