Synthesis of acrimarins from 1,3,5‐trioxygenated‐9‐acridone derivatives | Zendy

Herath H. M. T. B. | Zendy; Müller K. | Zendy; Diyabalanage H. V. K. | Zendy

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

Author(s) -

Herath H. M. T. B.,

Müller K.,

Diyabalanage H. V. K.

Publication year - 2004

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570410104

Subject(s) - acridone , chemistry , phloroglucinol , demethylation , coumarin , stereochemistry , methylation , condensation , organic chemistry , gene , physics , thermodynamics , biochemistry , gene expression , dna methylation

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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