FeCl3·6H2O-Catalyzed Tandem Alkylation–Hydrolysis Reaction of Chain α-Oxo Ketene Dithioacetals with Alcohols: Efficient ­Synthesis of α-Alkylated β-Oxo Thioesters

Abstract

A novel FeCl3·6H2O-catalyzed tandem Friedel–Crafts alkylation–hydrolysis reaction between chain α-oxo ketene dithioacetals and alcohols to afford α-alkylated β-oxo thioesters has been successfully developed. The reaction is efficient in the presence of catalyst loading as low as 30 mol% in MeCN at room temperature, and a wide variety of α-alkylated β-oxo thioesters are efficiently synthesized in good yields.

Green Tandem [5C + 1C] Cycloaromatization of α-Alkenoyl Ketene Dithioacetals and Nitroethane in Water: Eco-Friendly Synthesis of Ortho-Acylphenols

“…In view of the importance of ortho-acylphenols and our ongoing interests in aqueous organic synthesis 18 and the synthetic application of α-oxo ketene dithioacetals, 19 we recently researched in detail tandem [5C + 1C] annulations of α-alkenoyl ketene dithioacetals and nitroethane in water to prepare ortho-acylphenols. It was found that there were tandem Michael addition/cyclization/aromatization reactions between α-alkenoyl ketene dithioacetals and nitroethane in the presence of 2.0 equivalents of DBU in boiling water, affording orthoacylphenols in excellent yields (Scheme 1).…”

Synthesis of Polysubstituted 2,3-Dihydropyridin-4(1H)-one in Water

“…因此, 发展符合绿色 化学理念的 2,3-二氢-4-吡啶酮的水相合成是非常必要 的. 文献研读可知, 虽然已经发展多种关于含氮杂环化 合物的绿色合成方法 [36][37][38] , 但迄今为止还没有关于 2,3-二氢-4-吡啶酮的水相合成研究的报道.近些年来, 在研究二硫缩烯酮的合成与应用研究 中 [39][40][41] , 我们研究组也一直进行它们的水相反应研究, 已经取得一定成果, 成功地实现了无气味的 α-羰基二硫 缩烯酮作代硫醇试剂与醛或酮的水相硫缩醛/酮化反 应 [42] 、二硫缩烯酮与醇的水相 Friedel-Crafts 烷基化反 应 [43] 、二硫缩烯酮 [44] 和 β-吲哚基-β-乙硫基-α,β-不饱和…”

“…近些年来, 在研究二硫缩烯酮的合成与应用研究 中 [39][40][41] , 我们研究组也一直进行它们的水相反应研究, 已经取得一定成果, 成功地实现了无气味的 α-羰基二硫 缩烯酮作代硫醇试剂与醛或酮的水相硫缩醛/酮化反 应 [42] 、二硫缩烯酮与醇的水相 Friedel-Crafts 烷基化反 应 [43] 、二硫缩烯酮 [44] 和 β-吲哚基-β-乙硫基-α,β-不饱和…”