Inspired
by the success of fluorinated corticosteroids in the 1950s
and fluoroquinolones in the 1980s, fluorine-containing pharmaceuticals,
which are also known as fluoro-pharmaceuticals, have been attracting
attention for more than half of a century. Presently, about 20% of
the commercial pharmaceuticals are fluoro-pharmaceuticals. In this
mini-review, we analyze the prevalence of fluoro-pharmaceuticals in
the market and categorize them into several groups based on the chemotype
of the fluoro-functional groups, their therapeutic purpose, and the
presence of heterocycles and/or chirality to highlight the structural
motifs, patterns, and promising trends in fluorine-based drug design.
Our database contains 340 fluoro-pharmaceuticals, from the first fluoro-pharmaceutical,
Florinef, to the latest fluoro-pharmaceuticals registered in 2019
and drugs that have been withdrawn. The names and chemical structures
of all the 340 fluorinated drugs discussed are provided in the Supporting
Information.
The first example of the synthesis of β-lactam-triflones is described. Treatment of 2-diazo-1-aryl-2-(trifluoromethylsulfonyl)ethanones 1c-f with imines 2 under catalyst-free heating conditions provides pharmaceutically attractive multisubstituted β-lactam-triflones 3 in good to high yields with regio- and diastereoselectivities. A successive Wolff rearrangement and Staudinger [2 + 2] cycloaddition reaction are key elements for the success of this transformation.
Here we have successfully demonstrated the first stereodivergent direct nucleophilic trifluoromethylation of N-sulfinylimines using the potent greenhouse gas "HFC-23, fluoroform" with an organic-superbase or an organometallic-base in high yields and selectivity.
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