Reaction of pyrroles with naphthoquinones. Synthesis of new pyrrolylnaphthoquinone dyes

✍ Scribed by Claude Lion; Richard Baudry; Mir Hedayatullah; Louis Da Conceição; Michel Hocquaux; Sylvie Genard; Jean Maignan

• Book ID: 102344295
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 433 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370638

✦ Synopsis

Abstract

The reaction of 1,4‐naphthoquinone (1) with N‐alkylpyrroles (2) gives a mixture of 2‐(pyrrol‐2‐yl)‐1,4‐naphthoquinones (3) and 2,5‐bis(1,4‐naphthoquinon‐2‐yl)pyrroles (4). The yields and the ratios of these two products depend greatly on the experimental conditions. The reaction has been extended to 5‐hydroxy‐1,4‐naphthoquinone (juglone, 5) and 1,2‐naphthoquinone (6). New pyrrolylnaphthoquinones are obtained.