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Synthesis of acrimarins from 1,3,5-trioxygenated-9-acridone derivatives

✍ Scribed by H. M. T. B. Herath; K. Müller; H. V. K. Diyabalanage

Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
180 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

1,3,5‐Trihydroxy‐9(10__H__)‐acridinone (1) was prepared from 3‐hydroxyanthranillic acid with phloroglucinol. 1,3‐Dihydroxy‐5‐methoxy‐9(10__H__)‐acridinone (2) was prepared from 3‐methoxyanthranillic acid and phloroglucinol. Methylation of 1 under different conditions gave 1‐hydroxy‐3,5‐dimethoxy (3), 1‐hydroxy‐3,5‐dimethoxy‐10‐methyl (4), 1‐hydroxy‐3,5‐dimethoxy‐4‐methyl (5), 1,3,5‐trimethoxy‐10‐methyl (6) and 1,3,5‐trimethoxy‐4,10‐dimethyl (7) analogues. Demethylation of 4 afforded the 1,3,5‐trihydroxy‐10‐methyl analogue 8. Condensation of acridones 1, 2, 3 and 4 individually with E‐suberenol (9) gave four novel acrimarins (acridone‐coumarin dimers) 10, 11, 12 and 13 respectively, while the acridone 8 gave previously reported acrimarin‐G (14).

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