Direct synthesis of 2-/3-(trifluoromethyl)thiochroman-4-ones: Superacid-induced tandem alkylation-cyclic acylation of benzenethiols using 2-/3-(trifluoromethyl)acrylic acid

作者：Prakash G K Surya; Narayanan Arjun; Nirmalchandar Archith; Vaghoo Habiba; Paknia Farzaneh; Mathew Thomas; Olah George A

来源：Journal of Fluorine Chemistry, 2017, 196: 63-66.

DOI：10.1016/j.jfluchem.2016.08.013

• Superelectrophilic activation
• Benzenethiols
• Trifluoromethanesulfonic acid
• Thiochromanones
• Fluoroorganics

Incorporation of fluorinated heterocyclic framework into organic molecules results in profound changes in their physical, chemical and biological properties. Realizing that the fluorinated thiochroman-4-ones are important scaffolds in medicinal chemistry and are rare in the chemical literature, one-pot synthesis of 2-/3-(trifluoromethyl)thiochroman-4-ones was attempted. Direct access to 2-/3-(trifluoromethyl) thiochroman-4-ones was achieved by a tandem allcylation-cyclic acylation process promoted by superelectrophilic activation of 2-/3-(trifluoromethyl)acrylic acid in superacidic trifluoromethanesulfonic acid under microwave-assisted Friedel-Crafts alkylation of benzenethiols followed by cyclization (via intramolecular acylation). Synthesis of a series of 2-13-(trifluoromethyl)thiochroman-4-ones from protosolvated 2-/3-(trifluoromethyl)acrylic acid intermediates and benzenethiols is described.

• 出版日期2017-4