|標題:||Regioselective Synthesis of Angular Isocoumarinselenazoles: A Benzoselenazole-directed, Site-specific, Ruthenium-catalyzed C(sp(2))-H Activation|
Salunke, Deepak B.
Department of Applied Chemistry
|關鍵字:||Selenourea;benzoselenazoles;C-H activation;isocoumarin;chelate-assisted;acid-alkyne insertion;catalyzed ruthenium|
|摘要:||The synthesis of new, angular isocoumarinselenazoles is described, which involves the construction of 2-amino benzoselenazoles and their regioselective C2N-alkylation and alkyne insertion. An expeditious and metal-free synthesis of 2-aminobenzoselenazoles by the reaction of methyl 3-amino-4-fluorobenzoate and isoselenocyanates was achieved. Further N-alkylation of the 2-aminobenzoselenazoles resulted the formation of two regioisomers with different reactivities towards the alkyne insertion. The regioselective construction of the a-pyrone ring on the benzo[1,3-d] selenazole skeleton was achieved via a ruthenium (II)-catalyzed oxidative annulation. It is clear that the selenazole nitrogen plays an important role in the observed selectivity.|
|期刊:||ADVANCED SYNTHESIS & CATALYSIS|
|Appears in Collections:||Articles|