A highly efficient methodology for the preparation of N-methoxycarbazoles and the total synthesis of 3,3'-[oxybis(methylene)]bis(9-methoxy-9H-carbazole)
Yongxin Zhang, Shucheng Wang, Yaodong Huang()
Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China
A convenient and highly efficient method is described for the synthesis of N-methoxycarbazole derivatives, including those with sterically demanding, benzannulated, or strongly electron-donating or -withdrawing substituents. Various N-methoxycarbazole derivatives were directly prepared in good-to-moderate yields by the Pd2(dba)3CHCl3/9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene-catalyzed reactions of the corresponding dibromobiphenyl compounds and methoxya-mine. Based on this methodology, the first total synthesis of 3,3′-[oxybis(methylene)]bis(9-methoxy-9H-carbazole), an antimicrobial dimeric carbazole alkaloid previously isolated from the stem bark of Murraya koenigii, was achieved in 18% yield over seven steps from 1,2-dibromobenzene.
. [J]. Frontiers of Chemical Science and Engineering, 2021, 15(3): 679-686.
Yongxin Zhang, Shucheng Wang, Yaodong Huang. A highly efficient methodology for the preparation of N-methoxycarbazoles and the total synthesis of 3,3'-[oxybis(methylene)]bis(9-methoxy-9H-carbazole). Front. Chem. Sci. Eng., 2021, 15(3): 679-686.
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