Synthesis of N<sub>1</sub>‐substituted coumarino[4,3‐c] pyrazoles

Čačić, Milan; Trkovnik, M.; Has‐Schön, Elizabeta

doi:10.1002/jhet.5570400513

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Cited by 10 publications

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Synthesis of N₁‐Substituted Coumarino[4,3‐c]pyrazoles.

2004

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Synthesis of N 1 -Substituted Coumarino[4,3-c]pyrazoles. -Title compounds (III), (V) and (VII) are prepared in moderate to high yields by condensation of 3-acyl-4-hydroxychromones with appropriate hydrazides. Compounds (III) are found to possess high antimicrobial activity against S. pneumoniae, whilst compounds (V) and (VII) show very weak activity against all the tested microorganisms. -(CACIC, M.; TRKOVNIK, M.; HAS-SCHOEN, E.; J.

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Synthesis of N₁‐Substituted Coumarino[4,3‐c]pyrazoles.

2004

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Efficient Synthesis of Fully Substituted and Diversely Functionalized Pyrazoles through p‐TSA Catalyzed One‐Pot Condensation of Cyclic β‐Diketones, Arylglyoxals and Arylhydrazones

Dhurey,

Mandal,

Pramanik

2023

Eur J Org Chem

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A one‐pot, three‐component, and atom economic synthesis of biologically and pharmaceutically important fully substituted and functionalized pyrazole derivatives has been accomplished under metal‐catalyst‐free benign conditions. The strategy involves early condensation of readily available cyclic β‐diketones (dimidone, 4‐hydroxycoumarin and 2‐hydroxy‐1,4‐naphthoquinone) and arylglyoxals to generate a chalcone type intermediate which upon acid catalyzed condensation with ambident nucleophile arylhydrazones produces various aryl and cyclic β‐diketone substituted pyrazole derivatives. The synthesis embraces high functional group tolerance, broad substrate scope, excellent yield of the products, short reaction time and operationally simple and mild reaction conditions. The synthesis provides an easy opportunity of incorporating biologically important N‐diarylsulfide/selenide functionality, various enolisable cyclic β‐diketones and other bioactive heterocycles concurrently to pyrazole, which may help in designing and development of pyrazole derivatives of pharmacological significance.

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