Efficient Synthesis of Novel Coumarin‐3‐carboxamides (=2‐Oxo‐2H‐1‐benzopyran‐3‐carboxamides) Containing Lipophilic Spacers |
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| Authors: | Saeed Balalaie Mohammad Ali Bigdeli Enayatollah Sheikhhosseini Azizollah Habibi Hamed Piri Moghadam Mehrnoush Naderi |
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| Affiliation: | 1. Peptide Chemistry Research Center, K.?N. Toosi University of Technology, P.O. Box 15875‐4416, Tehran, Iran (fax: +98‐21‐22853650);2. Faculty of Chemistry, Tarbiat Moallem University, No.?49, Mofateh Ave., Tehran, Iran;3. Faculty of Science, Department of Chemistry, Islamic Azad University, Kerman Branch, Kerman, Iran;4. Department of Chemistry, Sharif University of Technology, Tehran, Iran |
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| Abstract: | 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 CHCl3. |
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| Keywords: | Coumarin‐3‐carboxamides Ugi reaction Fluorescence Multicomponent reactions |
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