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Efficient synthesis of novel coumarin-3-carboxamides (=2-oxo-2h-1- benzopyran-3-carboxamides) containing lipophilic spacers

Balalaie, S ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1002/hlca.201100238
  3. Abstract:
  4. The novel coumarin-3-carboxamides (=2-oxo-2H-1-benzopyran-3-carboxamides) 5a-5g containing lipophilic spacers were synthesized through the Ugi-four-component reaction (Scheme 1). The reactions of aromatic aldehydes 1, 4,4'-oxybis[benzenamine] or 4,4'-methylenebis[benzenamine] as diamine 2, coumarin-3-carboxylic acid (=2-oxo-2H-benzopyran-3-carboxylic acid; 3), and alkyl isocyanides 4 lead to the desired substituted coumarin-3-carboxamides 5a-5g at room temperature with high bond-forming efficiency. These novel coumarin derivatives exhibit brilliant fluorescence at 544 nm in CHCl 3
  5. Keywords:
  6. Coumarin-3-carboxamides ; Fluorescence ; Multicomponent reactions ; Ugi reaction ; Aromatic aldehyde ; Bond forming ; Coumarin derivatives ; Efficient synthesis ; Isocyanides ; Room temperature ; Aldehydes ; Carboxylic acids ; Cyanides ; 2 oxo 2h 1 benzopyran 3 carboxamide derivative ; 4,4' methylenebis(benzenamine) ; 4,4' oxybis(benzenamine) ; Aldehyde derivative ; Alkyl group ; Amide ; Benzopyran derivative ; Coumarin 3 carboxamide derivative ; Coumarin 3 carboxylic acid ; Coumarin derivative ; Diamine ; Unclassified drug ; Carbon nuclear magnetic resonance ; Chemical bond ; Chemical procedures ; chemical reaction ; Drug structure ; Drug synthesis ; Electrospray mass spectrometry ; Lipophilicity ; Priority journal ; Proton nuclear magnetic resonance ; Reaction analysis ; Reproducibility
  7. Source: Helvetica Chimica Acta ; Volume 95, Issue 3 , 2012 , Pages 528-535 ; 0018019X (ISSN)
  8. URL: http://onlinelibrary.wiley.com/doi/10.1002/hlca.201100238/abstract?systemMessage=Wiley+Online+Library+will+be+unavailable+on+Saturday+27th+February+from+09%3A00-14%3A00+GMT+%2F+04%3A00-09%3A00+EST+%2F+17%3A00-22%3A00+SGT+for+essential+maintenance.++Apologies+for+the+inconvenience