A general and efficient synthesis of 5, 6-dihydrodibenzo[b, h][1, 6]naphthyridine derivatives. Issue 49 (7th December 2016)

• Record Type: Journal Article
• Authors: Dobrowolski, Jeremy C.; Katen, Alice; Fraser, Benjamin H.; Bhadbhade, Mohan; Black, David StC.; Kumar, Naresh
• Is Part Of: Tetrahedron letters. Volume 57:Issue 49(2016)
• Page Start: 5442
• Page End: 5445
• Publication Date: 2016-12-07
• Subjects: Dihydroquinolin-4-one -- Dihydrodibenzo[b, h][1, 6]naphthyridines -- Acid-catalyzed synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.10.067
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Nitrogen heterocycles related to the anti-malarial natural product dependensin. An efficient two-step synthesis of 5, 6-dihydrodibenzo[ b, h ][1, 6]naphthyridines. Synthesis of 13 novel 6, 7-diphenyl-5, 6-dihydrodibenzonaphthyridine derivatives. Benzonaphthyridine fluorescence emission maximum is dependent on solvent polarity. Abstract: A two-step procedure for the synthesis of dihydrodibenzonaphthyridine derivatives from benzaldehydes and 2-aminoacetophenones, proceeding through a substituted dihydroquinolone intermediate, is described. The synthetic protocol allows for a versatile and robust coupling method between a range of 2-aminoacetophenones or 2-aminobenzophenones and a selection of substituted dihydroquinolones.