Electrochemical synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives.
The 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives have been synthesized by direct electrochemical oxidation of catechols in the presence of 4-mercaptocoumarin as a nucleophile in water/acetonitrile (50/50) solution, in a one-pot process, at carbon rod electrode, in an undivided cell and in constant current conditions, through an EC mechanism. The products are characterized by spectra data. Besides, the difference in electrochemical oxidation of catechol in the presence of 4-hydroxycoumarin and 4-mercaptocoumarin explained by computational structure, natural bond orbital (NBO) analysis and density functional theory (DFT: B3LYP/6-31G*//B3LYP/6-31G*) based methods, using the GAUSSIAN 98 package of programs.
Nematollahi
Davood
D
Faculty of Chemistry, Bu-Ali-Sina University, Iran. nemat@basu.ac.ir
Azizian
Javad
J
Sargordan-Arani
Mohsen
M
Hesari
Mahdi
M
Jameh-Bozorghi
Saeed
S
Alizadeh
Abdolhamid
A
Fotouhi
Lida
L
Mirza
Behrooz
B
D015110:4-Hydroxycoumarins / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis*; D002396:Catechols / Q000737:chemistry; D004563:Electrochemistry; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D015110:4-Hydroxycoumarins; D001578:Benzopyrans; D002396:Catechols; D007202:Indicators and Reagents; C034221:catechol; C068805:4-hydroxycoumarin