Synthesis of novel 6,6'-methylene-bis-[3-(2-anilinoacetyl)-4-hydroxycoumarin] derivatives.
The synthesis of novel 6,6'-methylene-bis-[3-(2-anilinoacetyl)-4-hydroxycoumarin] derivatives 6a-f was achieved in excellent yields from 6,6'-methylene-bis-[3-(2-bromoacetyl)-4-hydroxycoumarin] 5 and various arylamines. 5,5'-Methylene-bis-ethylsalicylate 3 was obtained by the esterfication of 5,5'-methylene-bis-salicylic acid 2 with ethanol, which was in turn obtained from salicylic acid 1 and formaldehyde. Cyclocondensation of 3 with ethyl acetoacetate resulted in 6,6'-methylene-bis-[3-acetyl-4-hydroxycoumarin] 4, which on selective alpha-bromination with molecular bromine in the presence of montmorillonite K10-AlCl(3) catalyst, in chloroform-ethyl acetate binary solvent mixture at room temperature, afforded the compound 5 in excellent yield. All the newly synthesized compounds were characterized by their spectral data.
Sanjeeva Reddy
Cherkupally
C
Department of Chemistry, Kakatiya University, Warangal, India. chsrkuc@yahoo.co.in
Raghu
Mekala
M
D000085:Acetates; D002725:Chloroform; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared
C534255:6,6'-methylene-bis-(3-(2-anilinoacetyl)-4-hydroxycoumarin); D000085:Acetates; D003374:Coumarins; D007202:Indicators and Reagents; C007650:ethyl acetate; D002725:Chloroform