Montmorillonite-KSF mediated one step synthesis of pyranochromene derivatives

One-pot three-component reaction of substituted aromatic aldehydes, 2-cyanoacetamide and 4-hydroxycoumarin in the presence of Montmorillonite-KSF (MKSF) in ethanol results in the formation of pyrano[3,2-c]chromene-3-carboxylates (5a-m) has been described. The reaction was tested in different alcohol...

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Bibliographic Details
Published in:Journal of molecular structure 2018-11, Vol.1171, p.747-754
Main Authors: Subbareddy, Chitreddy V., Subashini, Radhakrishnan, Sumathi, Shanmugam
Format: Article
Language:English
Subjects:
4-Hydroxycoumarin
Aromatic aldehydes
Heterogeneous catalyst
Montmorillonite KSF (MKSF)
Multicomponent reaction
Pyrano[3,2-c]chromene
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Summary:One-pot three-component reaction of substituted aromatic aldehydes, 2-cyanoacetamide and 4-hydroxycoumarin in the presence of Montmorillonite-KSF (MKSF) in ethanol results in the formation of pyrano[3,2-c]chromene-3-carboxylates (5a-m) has been described. The reaction was tested in different alcohols, afforded pyrano [3,2-c] chromene-3-carboxylates (5a-m) of the corresponding alcohols in good yield. The mechanism reveals that the alcohol (as solvent) plays a major role in the inter conversion of amide to the corresponding esters with Montmorillonite KSF (M-KSF) as a catalyst. Excellent yields, inexpensive and readily available substrates, environmentally benign reaction condition, shorter reaction time, and easy workup are the major advantageous features of this protocol. [Display omitted] •Montmorillonite-KSF is an effective heterogeneous catalyst.•Easy to handle and simple reaction procedure.•Cost effective and high yields were observed in shorter reaction time.•Reusability of catalyst.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2018.06.052