50885-06-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Naphthalenamine, 1,4-dimethoxyis used as an intermediate in the synthesis of disubstituted naphthoimidazoles for their potential anti-inflammatory properties. These compounds can be further developed into effective therapeutic agents for the treatment of various inflammatory conditions.

Upstream product

• 50885-07-9 1,4-dimethoxy-2-nitronaphthalene 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 571-60-8 1,4-Dihydroxynaphthalene 

Downstream Products

• 89767-40-8 (Z)-ethyl phenylpyruvate 2-<(1,4-dimethoxy-2-naphthyl)hydrazone> 
• 89767-41-9 (E)-ethyl phenylpyruvate 2-<(1,4-dimethoxy-2-naphthyl)hydrazone> 

Relevant academic research and scientific papers

Synthesis of kalasinamide, a putative plant defense phototoxin

The first total synthesis of the azaanthracene kalasinamide (1) is described, and the discrepancy in the reported 13C NMR data and melting points for the natural product from two different sources is resolved. Kalasinamide is prone to autosensitized photooxidation, in solution and in the solid state, to give the corresponding quinone, marcanine A (8). This transformation may be representative of a novel and more general step in the biosynthesis of (aza)anthraquinones. Through its ability to generate toxic singlet oxygen, kalasinamide may serve a protective role, defending the plant against predation and the invasion of microbial pathogens, following mechanical insult.

Photoelectrocyclization Reactions of Amidonaphthoquinones

Readily available acrylamide naphthoquinones can be converted into the corresponding aza-anthraquinones using 6?-photoelectrocyclization reactions. Not only do these reactions not proceed thermally but, as demonstrated here, they can also be used to generate a range of aza-anthraquinone and aza-tetracycline derivatives including the natural products griffithazanone A and marcanine A. Several of the aza-anthraquinones generated in this work showed antibacterial activity.

Hypervalent iodine-induced nucleophilic substitution of para-substituted phenol ethers. Generation of cation radicals as reactive intermediates

A novel hypervalent iodine induced nucleophilic substitution of para-substituted phenol ethers in the presence of a variety of nucleophiles is described. UV and ESR spectroscopic studies indicate that this reaction proceeds via cation radicals, [ArH?+], as reactive intermediates generated by single-electron transfer (SET) from a charge-transfer (CT) complex of phenol ethers with phenyliodine(III) bis(trifluoroacetate) (PIFA). This is the first case that involves a radical intermediate on hypervalent iodine oxidations of aromatic compounds.