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Issue 110, 2016, Issue in Progress
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La(OTf)3 catalyzed reaction of salicylaldehyde phenylhydrazones with β-ketoesters and activated alkynes: facile approach for the preparation of chromenopyrazolones

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Abstract

A facile approach has been developed for the preparation of chromenopyrazolones (5a–o, 7a–k) by the reaction of salicylaldehyde phenylhydrazones (3a–o) with β-ketoesters (4a, 4f–g) and activated alkynes (6a–e) in the presence of La(OTf)3 with good yields. However, the reaction of salicylaldehyde phenylhydrazones (3a, 3c, 3j–k, 3n) with ethyl 4-chloro-3-oxobutanoate (4e) underwent cyclization with reductive dechlorination and provided the methyl chromenopyrazolones instead of chloromethyl chromenopyrazolones. The present solvent free protocol provided the novel heterocyclic compounds.

Graphical abstract: La(OTf)3 catalyzed reaction of salicylaldehyde phenylhydrazones with β-ketoesters and activated alkynes: facile approach for the preparation of chromenopyrazolones

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Supplementary files

Article information


Submitted
30 Aug 2016
Accepted
07 Nov 2016
First published
08 Nov 2016

RSC Adv., 2016,6, 108654-108661
Article type
Paper

La(OTf)3 catalyzed reaction of salicylaldehyde phenylhydrazones with β-ketoesters and activated alkynes: facile approach for the preparation of chromenopyrazolones

K. S. Hariprasad, K. V. Prasad and B. C. Raju, RSC Adv., 2016, 6, 108654
DOI: 10.1039/C6RA21717F

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