Quinone-amine reactions, XX: 1,4-Naphthoquinone derivatives of psychopharmacological agents with secondary amine structure

Article abstract of DOI:10.1002/ardp.19863190708

Desipramine-like secondary amines (A-D) react with 1,4-naphthoquinone to give the 2-amino-1,4-naphthoquinone derivatives 3a-d, which are N-dealkylated by daylight. The nortriptyline derivative 3b additionally gives the blue dehydrogenated compound 6. 2-Amino-3-methyl-1,4-naphthoquinone 16a was not obtained from 2-methyl-1,4-naphthoquinone (7) and desipramine (A), whereas 2-bromo-3-methyl-1,4-naphthoquinone (13) and 2-methyl-2,3-epoxy-1,4-naphthoquinone (15) react with A to yield 16a. The amine function neighboring the methyl group in 16a produces a bathochromic effect of 44 nm.