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TITLE:
Ferrocene anchored activated carbon as a versatile catalyst for the synthesis of 1,5-benzodiazepines via one-pot environmentally benign conditions - imarina:9262469

URV's Author/s:Nabgan, Walid
Author, as appears in the article.:Kusuma, Suman; Patil, Komal N.; Srinivasappa, Puneethkumar M.; Chaudhari, Nitin; Soni, Ajay; Nabgan, Walid; Jadhav, Arvind H.;
Author's mail:walid.nabgan@urv.cat
Author identifier:0000-0001-9901-862X
Journal publication year:2022
Publication Type:Journal Publications
APA:Kusuma, Suman; Patil, Komal N.; Srinivasappa, Puneethkumar M.; Chaudhari, Nitin; Soni, Ajay; Nabgan, Walid; Jadhav, Arvind H.; (2022). Ferrocene anchored activated carbon as a versatile catalyst for the synthesis of 1,5-benzodiazepines via one-pot environmentally benign conditions. Rsc Advances, 12(23), 14740-14756. DOI: 10.1039/d2ra00202g
Papper original source:Rsc Advances. 12 (23): 14740-14756
Abstract:1,5-Benzodiazepine is considered as one of the central moieties in the core unit of most drug molecules. Construction of such moieties with a new C-N bond under solvent-free and mild reaction conditions is challenging. Herein, we present a benign protocol for one pot synthesis of 1,5-benzodiazepine derivatives by using ferrocene (FC) supported activated carbon (AC) as a heterogeneous catalyst. The catalyst FC/AC was characterized by several analytical and spectroscopic techniques to reveal its physicochemical properties and for structural confirmation. The synthesized catalyst FC/AC was explored for its catalytic activity in the synthesis of 1,5-benzodiazepines through condensation of o-phenylenediamine (OPDA) and ketones (aromatic and aliphatic) under solvent-free conditions. The robust 10 wt% FC/AC catalyst demonstrated appreciable activity with 99% conversion of diamines and 91% selectivity towards the synthesis of the desired benzodiazepine derivatives under solvent-free conditions at 90 degrees C in 8 h. Additionally, several reaction parameters such as catalyst loading, reaction temperature, effect of reaction time and effect of different solvents on selectivity were also studied and discussed in-depth. To understand the scope of the reaction, several symmetrical and unsymmetrical ketones along with different substituted diamines were tested with the synthesized catalyst. All prepared reaction products were obtained in good to efficient yields and were isolated and identified as 1,5-benzodiazepines and no side products were observed. The obtained catalyst characterization data and the activity studies suggested that, the synergetic effect occurred due to the uniform dispersion of ferrocene over the AC surface with numerous acidic sites which triggered the reaction of diamine and ketone to form the corresponding benzodiazepine derivative and the same was illustrated in the plausible mechanism. Furthermore, the synthesized catalyst was tested for leaching and recyclability, and the results confirmed that catalyst can be used for up to six consecutive cycles without much loss in the catalytic activity and its morphology which makes the process sustainable and economical for scale-up production. The present method offered several advantages such as an ecofriendly method, excellent yields, sustainable catalytic transformation, easy work-up and isolation of products, and quick recovery of catalyst.
Article's DOI:10.1039/d2ra00202g
Link to the original source:https://pubs.rsc.org/en/content/articlelanding/2022/ra/d2ra00202g
Papper version:info:eu-repo/semantics/publishedVersion
licence for use:https://creativecommons.org/licenses/by/3.0/es/
Department:Enginyeria Química
Licence document URL:https://repositori.urv.cat/ca/proteccio-de-dades/
Thematic Areas:Zootecnia / recursos pesqueiros
Saúde coletiva
Química
Odontología
Medicina veterinaria
Medicina iii
Medicina ii
Medicina i
Materiais
Interdisciplinar
Geociências
General chemistry
General chemical engineering
Farmacia
Ensino
Engenharias iv
Engenharias iii
Engenharias ii
Engenharias i
Economia
Ciências biológicas iii
Ciências biológicas ii
Ciências biológicas i
Ciências ambientais
Ciências agrárias i
Ciência de alimentos
Ciência da computação
Chemistry, multidisciplinary
Chemistry (miscellaneous)
Chemistry (all)
Chemical engineering (miscellaneous)
Chemical engineering (all)
Biotecnología
Biodiversidade
Astronomia / física
Keywords:Triflate
Route
Reusable catalyst
Mild
Highly efficient
Graphene oxide
Facile
Derivatives
Complexes
3-component synthesis
Entity:Universitat Rovira i Virgili
Record's date:2024-09-07
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