Methylene Thiazolidinediones as Alkylation Reagents in Catalytic C-H Functionalization: Rapid Access to Glitazones
Youjung Byun1, Kyeongwon Moon1, Jihye Park1
1School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
Abstract:
The straightforward and rapid incorporation of a thiazolidinedione scaffold into prefunctionalized (hetero)aromatic compounds is in demand for the development of antidiabetic glitazones and other pharmaceuticals. Herein, we report the unprecedented N- and O-directed C-H alkylation of various (hetero)arenes with methylene thiazolidinediones under rhodium(III) catalysis. The applicability of the developed protocol in challenging contexts is exhibited by the late-stage installation of a methylene thiazolidinedione moiety on the C-H bond of commercially available drug molecules. Combined mechanistic investigations aided the elucidation of a plausible reaction mechanism.
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