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

Biswanath Das; Nikhil Chowdhury; Kongara Damodar; Joydeep Banerjee

doi:10.1248/cpb.55.1274

Notes

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

Biswanath Das, Nikhil Chowdhury, Kongara Damodar, Joydeep Banerjee

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Keywords: Morita–Baylis–Hillman acetate, benzene thiol, (Z)-allyl sulfide, (E)-allyl sulfide, (Z)-3-(4-methoxybenzylidene)thiochroman-4-one, antifungal compound

JOURNAL FREE ACCESS

2007 Volume 55 Issue 8 Pages 1274-1276

DOI https://doi.org/10.1248/cpb.55.1274

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Abstract

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.

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