Beilstein J. Org. Chem.2024,20, 2704–2707, doi:10.3762/bjoc.20.227
-dihydro[1,3]thiazolo[4,5-b]pyridine derivatives that exhibited strong herbicidal activity against commercially significant grass weeds in preemergence greenhouse tests. The synthetic route for this new family of compounds was developed and optimized, involving several reaction steps, included Pd-catalyzed
intramolecular aminocarbonylation using Mo(CO)6. Both catalytic approaches successfully produced the desired DBDAPs.
As previously mentioned, organic synthesis is a crucial tool for preparing complex molecules of high value to industry. Frackenpohl et al. [13] designed and synthesized a new library of 2,3
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...