1203669-23-1Relevant articles and documents
Practical and versatile synthesis of thioflavones from 2-bromobenzoyl chlorides
Lee, Jae In,Choi, Jin Sun
, p. 253 - 256 (2015/06/16)
A practical and versatile synthesis of thioflavones from 2-bromobenzoyl chlorides as potent drug candidates, including derivatives with chloro, methyl, or methoxy substituents on the condensed benzene ring was reported. 4,6-Pyrimidyl di(2-halobenzoates)were readily prepared by acylation of 2 equiv of 1 with 4,6-dihydroxypyrimidine in the presence of 2 equiv of triethylamine in methylene chloride at room temperature. After evaporating methylene chloride, the mixture was dissolved in anhydrous THF and triethylamine hydrochloride was filtered off. The condensed residue was purified by short pathway silica gel column chromatography or recrystallization in 75% EtOAc/n-hexane to give 2 in 85-94% yields. Successful synthesis of 2 equiv of 1-(2-bromophenyl)-3-(hetero)aryl-2-propyn-1-ones was accomplished by reacting 1 equiv of 2 with 2 equiv of (hetero)arylethynylmagnesium bromides. Benzothiopyran ring formation was achieved via the 1,4-addition of hydrosulfide anion and one-pot sequence of bromide substitution. The reaction worked well with electron-withdrawing substituents, such as 7-chloro groups, and electrondonating substituents, such as 7-methyland 6-methoxy groups, in the condensed benzene rings.
Palladium-catalyzed tandem amination reaction for the synthesis of 4-quinolones
Zhao, Tlankun,Xu, Bin
supporting information; experimental part, p. 212 - 215 (2010/03/24)
(Figure presented) An efficient palladium-catalyzed tandem amlnatlon approach was developed In one step to afford functlonallzed 4-qulnolones In good to excellent ylelds from easlly accessible o-haloaryl acetylenlc ketones and primary amines.
