A highly efficient methodology for the preparation of N-methoxycarbazoles and the total synthesis of 3,3'-[oxybis(methylene)]bis(9-methoxy-9H-carbazole)  

作　　者：Yongxin Zhang Shucheng Wang Yaodong Huang 

机构地区：[1]Key Laboratory of Systems Bioengineering(Ministry of Education),School of Chemical Engineering and Technology,Tianjin University,Tianjin 300350,China

出　　处：《Frontiers of Chemical Science and Engineering》2021年第3期679-686,共8页化学科学与工程前沿（英文版）

基　　金：supported by the Natural Science Foundation of Tianjin,China(No.15JCYBJC20100).

摘　　要：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 Pd_(2)(dba)_(3)CHCl_(3)/9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene-catalyzed reactions of the corresponding dibromobiphenyl compounds and methoxyamine.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.

关 键 词：N-methoxyl carbazole dimeric N-methoxyl carbazole alkaloid total synthesis double N-arylation of methoxyamine 

分 类 号：O62[理学—有机化学]