Efficient atom-economic one-pot multicomponent synthesis of benzylpyrazolyl coumarins and novel pyrano[2,3-c]pyrazoles catalysed by 2-aminoethanesulfonic acid (taurine) as a bio-organic catalyst

• Published in: Synthetic communications Vol. 49; no. 17; pp. 2244 - 2257
• Main Authors: Chate, Asha V., Shaikh, Badrodin Ayyub, Bondle, Giribala M., Sangle, Sunil M.
• Format: Journal Article
• Language: English
• Published: PHILADELPHIA Taylor & Francis 02.09.2019; Taylor & Francis Ltd
• Subjects: 2-Aminoethanesulfonic acid; Aldehydes; benzylpyrazolyl coumarin; Catalysis; Catalysts; Chemistry; Chemistry, Organic; Coumarin; Economic conditions; green reaction; Hydrazines; Malononitrile; multicomponent reaction; Physical Sciences; pyrano[2,3-c]pyrazoles; Pyrazole; Reaction time; Science & Technology; ORGANIC-SYNTHESIS; pyrano; benzylpyrazolyl coumarin; green reaction; ANTITUMOR-ACTIVITY; CANCER; 3-c]pyrazoles; ANTIOXIDANT; GREEN SYNTHESIS; 4-HYDROXYCOUMARIN; CHEMISTRY; multicomponent reaction; 2-Aminoethanesulfonic acid; DERIVATIVES
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397911.2019.1619772

The present work describes eco-friendly multicomponent protocol for the synthesis in excellent yields of structurally diverse benzylpyrazolyl coumarin 5 (a-s) involving the reaction of 4-hydroxycoumarin, ethyl acetoacetate, hydrazine hydrate/phenyl hydrazine hydrate and aldehydes, also novel pyrano[2,3-c]pyrazole derivatives 8 (a-k) integrated by isonicotinic acid hydrazide from reaction of aldehyde, ethyl acetoacetate, malononitrile with isoniazid, employing water as a reaction medium and 2-aminoethanesulfonic acid (taurine) as the catalyst. This new methodology endowed the advantages such as short reaction time, recovery of catalysts after catalytic reaction and reusing them without losing their activity and alleviate of operation.