Beilstein J. Org. Chem.2024,20, 540–551, doi:10.3762/bjoc.20.46
, Bayer AG, Industriepark Höchst, 65926 Frankfurt am Main, Germany 10.3762/bjoc.20.46 Abstract The present work covers novel herbicidal lead structures that contain a 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine scaffold as structural key feature carrying a substituted phenyl side chain. These new compounds
introducing a nonaromatic motif via preparation of the novel 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines 7.
Results and Discussion
Although the 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine scaffold looks relatively simple at a first glance, it displays a very different reactivity compared to the parent naphthyridine
series. Likewise, 1,8-naphthyridines are easily accessed in high yield and on a multigram scale via Friedländer synthesis [18]. This was in clear contrast to the intermediate thiazolo[4,5-b]pyridines and the desired 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine that we wanted to access, with approaches to
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Graphical Abstract
Scheme 1:
Selected known inhibitors 1–3 of acyl-ACP thioesterases (belonging to the protein family of FATs) a...