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Efficient one-pot four-component synthesis and X-ray crystallographic structure of 2-pyridone derivatives

Balalaie, S ; Sharif University of Technology | 2013

2011 Viewed
  1. Type of Document: Article
  2. DOI: 10.1002/jhet.1632
  3. Publisher: 2013
  4. Abstract:
  5. A series of 3-cyano-2-pyridone derivatives were synthesized by one-pot four-component condensation reaction involving a benzaldehyde derivative, alkyl cyanoacetate, acyclic or cyclic ketones, and ammonium acetate in reflux condition. The X-ray structure of the products 5a and 5d confirm symmetric dimers via hydrogen bonding interactions between individual pyridine molecules showing, in addition, also π-π stacking interactions
  6. Keywords:
  7. 2 Pyridone derivative ; 3 Cyano 2 pyridone derivative ; 3 Cyano 4 (2 furyl) 5 phenyl 6 methyl 2(1h)pyridone ; 3 Cyano 4 (2 pyridyl) 5 phenyl 6 methyl 2(1h)pyridone ; 3 Cyano 4 (2 thienyl) 5 phenyl 6 methyl 2(1h)pyridone ; 3 Cyano 4 (3 nitrophenyl) 5,6 dimethyl 2(1h)pyridone ; 3 Cyano 4 (3 nitrophenyl) 6 isobutyl 2(1h)pyridone ; 3 Cyano 4 (3 nitrophenyl) 6 propyl 2(1h)pyridone ; 3 Cyano 4 (4 chlorophenyl) 5 phenyl 6 methyl 2(1h)pyridone ; 3 Cyano 4 (4 chlorophenyl) 5,6 (1,3 propanediyl) 2(1h)pyridone ; 3 Cyano 4 (4 chlorophenyl) 5,6 dimethyl 2(1h)pyridone ; 3 Cyano 4 (4 methylphenyl) 5,6 dimethyl 2(1h)pyridone ; 3 Cyano 4 (4 nitrophenyl) 5,6 dimethyl 2(1h)pyridone ; 3Cyano 4 (4 pyridyl) 5 phenyl 6 methyl 2(1h)pyridone ; 3 Cyano 4 phenyl 5,6 (1,4 butanediyl) 2(1h)pyridone ; 3 Cyano 4 phenyl 5,6 dimethyl 2(1h)pyridone ; 3 Cyano 4 phenyl 6 isobutyl 2(1h)pyridone ; 3 Cyano 4 phenyl 6 propyl 2(1h)pyridone ; 3Cyano 4,5 diphenyl 6 methyl 2(1h)pyridone ; Acetic acid derivative ; Ammonium acetate ; Benzaldehyde derivative ; cyanoacetate derivative ; Dimer ; Ketone derivative ; Unclassified drug ; Chemical interaction ; Chemical procedures ; Drug structure ; Drug synthesis ; Hydrogen bond ; One pot synthesis ; Polymerization ; Reaction analysis ; Reproducibility ; Structure analysis ; X ray crystallography
  8. Source: Journal of Heterocyclic Chemistry ; Volume 50, Issue 6 , 2013 , Pages 1272-1280 ; 0022152X (ISSN)
  9. URL: http://onlinelibrary.wiley.com/doi/10.1002/jhet.1632/abstract;jsessionid=C5D3692244EAFF68F1E4A6B683BD3EAA.f03t03