For the first time, an eco-friendly
and sustainable tandem [5C
+ 1C] cycloaromatization of α-alkenoyl ketene dithioacetals
and nitroethane in water for the efficient synthesis of ortho-acylphenols was reported. In refluxing water, a range of α-alkenoyl
ketene dithioacetals and nitroethane smoothly underwent tandem Michael
addition/cyclization/aromatization reactions in the presence of 2.0
equivalents of DBU to provide various ortho-acylphenols
in excellent yields. The green approach to ortho-acylphenols
not only avoided the use of harmful organic solvents, which could
result in serious environmental and safety issues, but also exhibited
fascinating features such as good substrate scope, excellent yields,
simple purification for desired products, ease of scale-up, and reusable
aqueous medium.
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