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Göteborgs universitets publikationer

Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds.

Författare och institution:
Kristian Dahlén (Institutionen för kemi); Erik A A Wallén (Institutionen för kemi); Morten Grøtli (Institutionen för kemi); Kristina Luthman (Institutionen för kemi)
Publicerad i:
The Journal of organic chemistry, 71 ( 18 ) s. 6863-6871
Artikel, refereegranskad vetenskaplig
Sammanfattning (abstract):
A useful and efficient synthetic strategy to 2,3,6,8-tetrasubstituted chromone derivatives has been developed. 2-Aryl/styryl-8-bromo-6-chloro-3-hydroxychromone derivatives were synthesized and used as scaffolds by introducing a variety of substituents in the 3-, 6-, and 8-positions using palladium-mediated reactions. Excellent regioselectivity in all positions could be obtained by performing reactions in the 8-position first, in which Stille, Heck, Suzuki, and Sonogashira reactions gave good to excellent yields of product (63-98%). Stille and Heck reactions in the 6-position also gave the desired products in good yields (64-86%). The hydroxy group in the 3-position was activated as a triflate and used in productive Stille reactions (63-94%). This hydroxyl group was also used in O-alkylation reactions with different functionalized alkyl bromides (57-88%). The flavonoids, which are based on the chromone structure, and other related ring systems, have several interesting biological activities. The chromones are also interesting structural scaffolds, and they have for example been designed to be used as mimetics of short peptides. The versatile applicability of chromone derivatives and especially their potential use in drug discovery implicates the importance of access to efficient synthetic routes to such compounds.
Ämne (baseras på Högskoleverkets indelning av forskningsämnen):
Medicinska grundvetenskaper ->
Chemistry, Organic, methods, Chromones, chemistry, Cross-Linking Reagents, chemistry, Flavones, chemistry, Molecular Structure, Palladium, chemistry
Postens nummer:
Posten skapad:
2007-10-15 16:40
Posten ändrad:
2012-01-26 11:14

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