Group-assisted purification (GAP) chemistry for dihydrofurans: water as a medium for catalyst free synthesis in a one pot four component reaction

A simple, catalyst free, water mediated, one pot four component, green protocol was developed for title compounds 7 starting from aromatic aldehydes (1), malononitrile (2), 1,3-diones (3) and N-chlorosuccinimide (NCS) in a sequential addition reaction at ambient temperature. The approach presented h...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2014-01, Vol.16 (6), p.3237-3246
Main Authors: Chennapuram, Madhu, Emmadi, Narender Reddy, Bingi, Chiranjeevi, Nanubolu, Jagadeesh Babu, Atmakur, Krishnaiah
Format: Article
Language:English
Subjects:
Aldehydes
Ambient temperature
Catalysts
Compatibility
Derivatives
Malononitrile
Purification
Synthesis
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Summary:A simple, catalyst free, water mediated, one pot four component, green protocol was developed for title compounds 7 starting from aromatic aldehydes (1), malononitrile (2), 1,3-diones (3) and N-chlorosuccinimide (NCS) in a sequential addition reaction at ambient temperature. The approach presented herein, for the first time, is through an unusual rearrangement where NCS was reacted with 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromen e-3-carbonitrile (4), which was formed by the Knoevenagel condensation of aldehyde and malononitrile followed by the Michael addition of 3. In addition, this novel protocol is compatible with various aldehydes and active C-H functional derivatives, accomplishes high yields and follows the GAP chemistry principle. Interestingly, compound 4 when reacted with NCS in alcohol medium gave 2-cyano-6,6-dimethyl-4-oxo-3-aryl-2,3,4,5,6,7-hexahydrobenzofuran- 2 -carboxylate (5).
ISSN:1463-9262
1463-9270
DOI:10.1039/c4gc00388h