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A direct FeCl3-catalyzed cross-coupling and cyclization reactions: A new approach to the construction of functionalized pyrano[3,2-a]carbazole derivatives

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Abstract The FeCl3-catalyzed cross-coupling through a sequential C−N and C−C bond-forming via tandem C−H and N−H bonds functionalization represents a novel method for the formation of dimeric carbazole derivatives. This… Click to show full abstract

Abstract The FeCl3-catalyzed cross-coupling through a sequential C−N and C−C bond-forming via tandem C−H and N−H bonds functionalization represents a novel method for the formation of dimeric carbazole derivatives. This approach provides a novel dimeric carbazole, namely murrabicine (4), from murrayacine (1). Following the same procedure, a cycloadduct (6) has been achieved due to different substitution pattern at the pyran ring of the mahanimbine (3). This strategy opens up an efficient and direct route to the formation of biologically important pyrano[3,2-a]carbazole alkaloids.

Keywords: fecl3 catalyzed; pyrano carbazole; carbazole derivatives; catalyzed cross; cross coupling

Journal Title: Tetrahedron
Year Published: 2017

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