Synthesis of 1-functionalized 5-methylnaphtho[2,3-g]isoquinoline-6,11-quinones

• Published in: Journal of organic chemistry Vol. 53; no. 22; pp. 5301 - 5304
• Main Authors: Croisy-Delcey, Martine, Rautureau, Marilys, Huel, Christiane, Bisagni, Emile
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.10.1988; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; One pot reaction; Condensation reaction; Nitrogen heterocycle; Quinone; Diels Alder addition; Tetracyclic compound; Aldehyde; Enol ester; Chemical substitution; Lithium Organic compounds; Chlorine Organic compounds; Conjugated dienic compound; Aromatic compound; Primary amine
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo00257a018

1-Chloro-5-methylnaphtho[2,3-g]isoquinoline-6,11-quinones were obtained through two independent pathways: (i) by Diels-Alder reaction of 1-chloro-5-methylbenzo[g]isoquinoline-6,9-quinone with 1,4-diacetoxybutadiene; (ii) by condensation of 2-formyl-1,4-dimethoxynaphthalenes with 4-acetyl-2-chloro-3-lithiopyridine ethylene glycol ketal and transformation of the resulting key intermediates by a reduction-hydrolysis-cyclization-demethylation-oxidation one-pot process. Whereas 1-substitution of 1-chloro-5-methylnaphtho[2,3-g]isoquinoline-6,11-quinone itself by amines took place cleanly, the corresponding 10-hydroxy derivative led to complex mixtures.