One-pot, green synthetic route for construction of coumarin C-4 bridged 2,6-dicyanoanilines and their photophysical study

A highly selective and more efficient green protocol has been developed via a one-pot, three-component approach for the synthesis of coumarin 2,6-dicyanoanilines in aqueous ethanol. From the mechanism, two molecules of malanonitrile condensed with aldehyde and ketone resulted in the adducts, which o...

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Bibliographic Details
Published in:Synthetic communications 2016-12, Vol.46 (24), p.2063-2072
Main Authors: Kulkarni, Rashmi C., Samundeeswari, S., Chougala, Bahubali M., Holiyachi, Megharaja, Kulkarni, Manohar V., Shastri, Lokesh A.
Format: Article
Language:English
Subjects:
2,6-Dicyanoanilines
4-formylcoumarins
malononitrile
multicomponent reactions
triethylamine
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Summary:A highly selective and more efficient green protocol has been developed via a one-pot, three-component approach for the synthesis of coumarin 2,6-dicyanoanilines in aqueous ethanol. From the mechanism, two molecules of malanonitrile condensed with aldehyde and ketone resulted in the adducts, which on intramolecular cyclization via two new C-C bonds formed to afford the title compound. The present methodology offers simplified purification and environmentally benign conditions, avoids the use of toxic solvents, and gives excellent yield with high purity. All the synthesized compounds have been characterized by spectral analysis. Optical and thermal screening studies of all newly synthesized compounds showed excellent photophysical and thermal stability properties.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2016.1245751