A wide‐ranging study of Suzuki reactions which use nitrogen‐containing heterocycles is described (see scheme; dba=dibenzylideneacetone, Cy=cyclohexyl). This method is highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2‐ and OH‐substituted substrates), and efficient even with unactivated aryl chlorides.
Eine umfassende Studie zu Suzuki‐Reaktionen mit Stickstoffheterocyclen wird vorgestellt (siehe Schema; dba=Dibenzylidenaceton, Cy=Cyclohexyl). Die Methode ist vielseitig (ein einziges Verfahren für alle Substrate einschließlich Boronatester und Trifluorborate), auf Substrate mit ungeschützten funktionellen Gruppen (NH2 und OH) anwendbar und auch für nichtaktivierte Arylchloride geeignet.
A series of novel 3-aryl-5-tert-butyl-4-chloro-4-oxazolin-2-ones (16) have been prepared and found to show significant herbicidal activity in the grams per are range against broadleaf and narrowleaf weeds. The key step in the introduction of the chlorine atom at the 4-position of the 4-chloro-4-oxazolin-2-one ring is dichlorination using chlorine gas and subsequent dehydrochlorination using diazabicyclo[5.4.0]undecene. 4-Alkylthio-and 4-methyl-4-oxazolin-2-one rings were synthesized from R-substituted R-bromopinacolone by cyclization reaction. Among the synthesized compounds, 5-tertbutyl-4-chloro-3-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-oxazolin-2-one (16h) showed the greatest activity against several weeds without damage to transplanted rice in the paddy field.
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