Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols
A metal-free access to 3-allyl-2-alkoxychromanones by PPh3-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.
Meng, Ling,Chang, Xiaoyong,Lin, Zhenyang,Wang, Jun (Joelle)
supporting information
p. 2663 - 2667
(2021/04/07)
KHMDS enhanced SmI2-mediated reformatsky type α-cyanation
A novel combination of SmI2, KHMDS, and TsCN can be utilized to introduce a cyano group into structurally diverse and highly sensitive 2-alkyl-chroman-4-ones. Subsequent oxidation allows the formed 2-alkyl-3-cyanochromones to be isolated in yields ranging from 49 to 77%. In addition, α-bromoketones and esters were found to undergo equally effective α-cyanation.
A mild and facile method for the synthesis of 3-cyano-chromones from oximes derived from 3-formylchromones using dimethylformamide-thionylchloride complex
A mild and facile method for the synthesis of 3-cyanochromones (4) from oximes (2) derived from 3-formylchromones using Dimethylformamide- thionylchloride complex (1) is herein reported.
Jagath Reddy,Latha,Srinivasa Rao
p. 279 - 282
(2007/10/03)
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