从森田-贝利斯-希尔曼乙酸酯温和高效地立体选择性合成(Z)-和(E)-烯丙基硫醚以及强效抗真菌剂(Z)-3-(4-甲氧基亚苄基)硫代色满-4-酮。

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.

作者信息

Das Biswanath, Chowdhury Nikhil, Damodar Kongara, Banerjee Joydeep

机构信息

Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, India.

出版信息

Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1274-6. doi: 10.1248/cpb.55.1274.

DOI:10.1248/cpb.55.1274

PMID:17666860

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.

摘要

通过在室温下于二甲基亚砜中，用苯硫酚在催化量的15%氢氧化钠水溶液和四丁基碘化铵存在下处理，从森田-贝利斯-希尔曼乙酸酯一锅法简便地立体选择性合成了(Z)-和(E)-烯丙基硫醚。该方法已应用于合成强效抗真菌化合物(Z)-3-(4-甲氧基亚苄基)硫代色满-4-酮。