Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3- f ] and [3,2- f ]indoles

A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3- f ] and [3,2- f ]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2022-03, Vol.24 (6), p.2429-2437
Main Authors: Sharapov, Ainur D., Fatykhov, Ramil F., Khalymbadzha, Igor A., Sharutin, Vladimir V., Santra, Sougata, Zyryanov, Grigory V., Chupakhin, Oleg N., Ranu, Brindaban C.
Format: Article
Language:English
Subjects:
Ambient temperature
Ball milling
Catalysts
Column chromatography
Green chemistry
Indoles
Ketoesters
Methanesulfonic acid
Phenols
Reaction time
Regioselectivity
Solvents
Synthesis
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Summary:A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3- f ] and [3,2- f ]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low E -factor. In contrast to traditional Pechmann condensation procedures, the mechanochemical protocol leads to the synthesis of pyranoindoles with excellent regioselectivity and high yields.
ISSN:1463-9262
1463-9270
DOI:10.1039/D1GC04564D