A Novel Approach for C–C, C–N, and C–O Bond Formation Reactions: A Facile Synthesis of Benzophenazine, Quinoxaline, and Phenoxazine Derivatives via Ring Opening of Benzoxepines

A new one-pot protocol has been developed for the synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives by the reaction of benzoxepine-4-carboxylates with benzene-1,2-diamines, ethane-1,2-diamine, and 2-aminophenols in the presence of Bi(OTf)3 (5 mol %) under mild conditions in very...

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Veröffentlicht in:Organic letters 2014-01, Vol.16 (2), p.420-423
Hauptverfasser: China Raju, Bhimapaka, Veera Prasad, Kasagani, Saidachary, Gannerla, Sridhar, Balasubramanian
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Sprache:eng
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Zusammenfassung:A new one-pot protocol has been developed for the synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives by the reaction of benzoxepine-4-carboxylates with benzene-1,2-diamines, ethane-1,2-diamine, and 2-aminophenols in the presence of Bi(OTf)3 (5 mol %) under mild conditions in very good yields. The present protocol opens a new way for C–C, C–N, and C–O bond-formation reactions in a single-step process. The structural assignment was confirmed by X-ray analysis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4033122