Novel methodology for the synthesis of the benzo[b]phenanthridine and 6H-dibenzo[c,h]chromen-6-one skeletons. Reactions of 2-naphthylbenzylamines and 2-naphthylbenzyl alcohols

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• 作者：Priyamvada Pradeep ; Kennedy J. Ngwira ; Chevonne Reynolds ; Amanda L. Rousseau ; Andreas Lemmerer¹ ; Manuel A. Fernandes¹ ; Myron M. Johnson ; Charles B. de Koning ; ^{charles.dekoning@wits.ac.za}
• 关键词：Benzo[b]phenanthridines ; Dibenzo[c ; h]chromen-6-ones ; Benzo[c]phenanthridines ; Suzuki-Miyaura reaction ; N-bromosuccinimide (NBS)
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：22 December 2016
• 年：2016
• 卷：72
• 期：51
• 页码：8417-8427
• 全文大小：923 K
• 卷排序：72

文摘

Novel syntheses of both the benzo[b]phenanthridine and the 6H-dibenzo[c,h]chromen-6-one motif are described. Reaction of (2-(3-bromo-1,4-dimethoxynaphthalen-2-yl)phenyl)methanamine with PIFA afforded benzo[b]phenanthridine-7,12-dione, while the related nonbrominated precursor, (2-(1,4,5-trimethoxynaphthalen-2-yl)phenyl)methanamine on treatment with PIFA, furnished the ortho-quinone 1-methoxybenzo[c]phenanthridine-11,12-dione. Unexpectedly, treatment of related oxygen analogs such as (2-(1,4-dimethoxynaphthalen-2-yl)phenyl)methanol with NBS under an O2 atmosphere, afforded a chromenone, 12-methoxy-6H-dibenzo[c,h]chromen-6-one.