A facile and green procedure in preparing dibenzo-chromeno-phenazine-diones using an effectual and recyclable Brønsted acidic ionic liquid

First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass, 13 C NMR, 19 F NMR, 1 H NMR and FT-IR data. Further, it was successfully applied in...

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Bibliographic Details
Published in:Scientific reports 2024-11, Vol.14 (1), p.26758-12, Article 26758
Main Authors: Hsu, Chou-Yi, Abdulkareem, Riyadh, Pallathadka, Harikumar, Abbot, Vikrant, Chahar, Mamata, Abduvalieva, Dilsora, Mustafa, Yasser Fakri, Altimari, Usama S., mhussan jabbar, Abeer, Zwamel, Ahmed Hussein
Format: Article
Language:English
Subjects:
639/638/309
639/638/403
639/638/77
Acids
Aldehydes
Benzene
Catalysts
Chemistry
Dibenzo-chromeno-phenazine-diones. Multicomponent domino reactions (MCDRs). 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT). Solvent-free medium
Fourier transforms
Humanities and Social Sciences
Hydrocarbons
Medical laboratories
multidisciplinary
NMR
Nuclear magnetic resonance
Pharmaceutical industry
Pharmacy
Phenazine
Science
Science (multidisciplinary)
Solvents
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Summary:First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass, 13 C NMR, 19 F NMR, 1 H NMR and FT-IR data. Further, it was successfully applied in the preparation of dibenzo-chromeno-phenazine-dione derivatives ( 1a - 12a , 9–15 min, 90–98%) via one-pot multicomponent domino reaction among 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes under optimal conditions (5 mol% of PBPBSDT, solvent-free, 60 °C). The proper reproducibility of the PBPBSDT homogeneous catalyst (5 times), solvent-free medium, reasonable TON (Turnover Number) and TOF (Turnover Frequency) numbers, the non-metallic framework of the catalyst, and the formation of C-N, C = N, C-C, C = C, C-O bonds in a single operation are the distinct advantages of this protocol.
ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-024-73257-3