A mild and efficient stereoselective synthesis of (Z)- and (E)-allyl sulfides and potent antifungal agent, (Z)-3-(4-methoxybenzylidene)thiochroman-4-one from Morita-Baylis-Hillman acetates.
A facile stereoselective synthesis of (Z)- and (E)-allyl sulfides has been accomplished from Morita-Baylis-Hillman acetates in one-pot by treatment with benzene thiol in the presence of catalytic amounts of 15% aqueous NaOH and TBAI in DMSO at room temperature. The method has been applied for the synthesis of (Z)-3-(4-methoxybenzylidene)thiochroman-4-one, a potent antifungal compound.
Das
Biswanath
B
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, India. biswanathdas@yahoo.com
Chowdhury
Nikhil
N
Damodar
Kongara
K
Banerjee
Joydeep
J
D000085:Acetates / Q000737:chemistry; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D004121:Dimethyl Sulfoxide; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012972:Sodium Hydroxide; D012997:Solvents; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis / Q000494:pharmacology
C522681:(Z)-3-(4-methoxybenzylidene)thiochroman-4-one; D000085:Acetates; D000498:Allyl Compounds; D000935:Antifungal Agents; D002839:Chromans; D007202:Indicators and Reagents; D012997:Solvents; D013440:Sulfides; D012972:Sodium Hydroxide; D004121:Dimethyl Sulfoxide