Natural product chemisrty, 143. Convenient synthesis of isoacronycine and some other new acridone derivatives
✍ Scribed by Reisch, Johannes ;Herath, H. M. T. Bandara ;Kumar, N. Savitri
- Book ID
- 102902293
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 555 KB
- Volume
- 1991
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The iodination of 1,3‐dihydroxy‐9‐acridone (1), 1‐hydroxy‐3‐methoxy‐10‐methyl‐9‐acridone (2) and 1,3‐dihydroxy‐10‐methyl‐9‐acridone (3) yields 1,3‐dihydroxy‐2,4‐diiodo‐9‐acridone (4), 1‐hydroxy‐2‐iodo‐3‐methoxy‐10‐methyl‐9‐acridone (5) and 1,3‐dihydroxy‐2‐iodo‐10‐methyl‐9‐acridone (6), respectively. The methylation of 4 and 5 gives 2,4‐diiodo‐1,3‐dimethoxy‐10‐methyl‐9‐acridone (7) and 2‐iodo‐1,3‐dimethoxy‐10‐methyl‐9‐acridone (9), respectively. The direct CC coupling of 2‐methyl‐3‐buten‐2‐ol to the compounds 5, 7 and 9 by palladium catalysed Heck condensation method gives three new acridone derivatives 1‐hydroxy‐2‐(3‐hydroxy‐3‐methyl‐1‐butenyl)‐3‐methoxy‐10‐methyl‐9‐acridone (10), 2,4‐bis(3‐hydroxy‐3‐methyl‐1‐butenyl)‐1,3‐dimethoxy‐10‐methyl‐9‐acridone (12) and 2‐(3‐hydroxy‐3‐methyl‐1‐butenyl)‐1,3‐dimethoxy‐10‐methyl‐9‐acridone (13) while compound 6 is converted into isonoracronycine (11). The methylation of 11 yields isoacronycine (14).