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ChemInform Abstract: Rapid Bergman Cyclization of 1,2-Diethynylheteroarenes.

✍ Scribed by Chang-Sik Kim; K. C. Russell


Book ID
101871892
Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Rapid Bergman Cyclization of 1,2-Diethynylheteroarenes.

-The synthesis of quinoxaline (III), pyridine (VI), and pyrimidine enediynes (IX) is achieved by palladium-catalyzed cross-coupling of the corresponding o-dihaloor o-halotriflic hetarenes (I), (V), and (VIII), resp., with trimethylsilylacetylene (II) in the presence of base. All enediynes undergo Bergman cyclization to afford the benzo-anellated analogues (IV), (VII), and (X), respectively. Kinetics of the cyclization is studied and compound (IX) is shown to possess remarkable reactivity. -(KIM, CHANG-SIK;


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