Reaction of pyrroles with naphthoquinones. Synthesis of new pyrrolylnaphthoquinone dyes

Authors
Lion, C Baudry, R Hedayatullah, M Da Conceicao, L Hocquaux, M Genard, S Maignan, J
Citation
C. Lion et al., Reaction of pyrroles with naphthoquinones. Synthesis of new pyrrolylnaphthoquinone dyes, J HETERO CH, 37(6), 2000, pp. 1635-1640
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
6
Year of publication
2000
Pages
1635 - 1640
Database
ISI
SICI code
0022-152X(200011/12)37:6<1635:ROPWNS>2.0.ZU;2-D
Abstract
The reaction of 1,4-naphthoquinone (1) with N-alkylpyrroles (2) gives a mix ture of 2-(pyrrol-2-yl)-1,4-naphthoquinones (3) and 2,5-bis(1,4-naphthoquin on-2-yl)pyrroles (4). The yields and the ratios of these two products depen d 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.