Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry

Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4 H -chromenes, tetrahydrospiro[chromene-3,4′-indoline], 2,2′-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tet...

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Bibliographic Details
Published in:Scientific reports 2023-01, Vol.13 (1), p.1386-17, Article 1386
Main Authors: Borah, Biplob, Swain, Sidhartha, Patat, Mihir, Kumar, Bhupender, Prajapat, Ketan Kumar, Biswas, Rathindranath, Vasantha, R., Chowhan, L. Raju
Format: Article
Language:English
Subjects:
639/638/224/685
639/638/77/889
Acids
Alzheimer's disease
Ambient temperature
Arthritis
Catalysts
Chemistry
Cyclohexane
Efficiency
Energy efficiency
Free energy
Humanities and Social Sciences
multidisciplinary
Organic solvents
Pharmaceutical industry
Science
Science (multidisciplinary)
Solvents
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Summary:Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4 H -chromenes, tetrahydrospiro[chromene-3,4′-indoline], 2,2′-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tetrahydro-1 H -xanthen-1-one by employing the reactivity of 5,5-dimethylcyclohexane-1,3-dione/cyclohexane-1,3-dione with TsOH⋅H 2 O as Brønsted acid catalyst under water-assisted grinding conditions at ambient temperature. The ability to accomplish multiple C–C, C=C, C–O, and C–N bonds from readily available starting materials via a domino multicomponent strategy in the absence of metal-catalyst as well as volatile organic solvents with an immediate reduction in the cost of the transformation without necessitates complex operational procedures, features the significant highlights of this approach. The excellent yield of the products, broad functional group tolerances, easy set-up, column-free, scalable synthesis with ultralow catalyst loading, short reaction time, waste-free, ligand-free, and toxic-free, are other notable advantages of this approach. The greenness and sustainability of the protocol were also established by demonstrating several green metrics parameters.
ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-023-27948-y