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Efficient Synthesis of Novel Coumarin‐3‐carboxamides (=2‐Oxo‐2 H ‐1‐benzopyran‐3‐carboxamides) Containing Lipophilic Spacers
Author(s) -
Balalaie Saeed,
Bigdeli Mohammad Ali,
Sheikhhosseini Enayatollah,
Habibi Azizollah,
Moghadam Hamed Piri,
Naderi Mehrnoush
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100238
Subject(s) - chemistry , coumarin , carboxylic acid , benzopyran , alkyl , fluorescence , medicinal chemistry , organic chemistry , physics , quantum mechanics
The novel coumarin‐3‐carboxamides (=2‐oxo‐2 H ‐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‐2 H ‐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 .