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. Issue 51 (22nd December 2016)

• Record Type: Journal Article
• Authors: Pradeep, Priyamvada; Ngwira, Kennedy J.; Reynolds, Chevonne; Rousseau, Amanda L.; Lemmerer, Andreas; Fernandes, Manuel A.; Johnson, Myron M.; de Koning, Charles B.
• Is Part Of: Tetrahedron. Volume 72:Issue 51(2016)
• Page Start: 8417
• Page End: 8427
• Publication Date: 2016-12-22
• Subjects: Benzo[b]phenanthridines -- Dibenzo[c, h]chromen-6-ones -- Benzo[c]phenanthridines -- Suzuki-Miyaura reaction -- N-bromosuccinimide (NBS); Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.10.071
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Novel syntheses of both the benzo[ b ]phenanthridine and the 6 H -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-6 H -dibenzo[ c, h ]chromen-6-one. Graphical abstract: