67879-20-3Relevant articles and documents
Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones
Kim, Hun Young,Song, Eunsun,Oh, Kyungsoo
supporting information, p. 312 - 315 (2017/04/21)
A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.
Ruthenium-NHC-catalyzed asymmetric hydrogenation of flavones and chromones: General access to enantiomerically enriched flavanones, flavanols, chromanones, and chromanols
Zhao, Dongbing,Beiring, Bernhard,Glorius, Frank
supporting information, p. 8454 - 8458 (2013/09/02)
Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O-heterocycles - flavanones, chromanones, flavanols, and chromanols - by means of an enantioselective Ru/NHC-catalyzed hydrogenation process (see scheme; NHC=N-heterocyclic carbene, PCC=pyridinium chlorochromate). Copyright
Photolysis of 3-bromochroman-4-ones
Consuelo Jiménez,Miranda, Miguel A.,Tormos, Rosa
, p. 339 - 347 (2007/10/03)
Photolysis of 3-bromochroman-4-ones (1a-f) leads to debrominated chromanones (2a-f) and chromones (3a-f) as major products. Their formation is accounted for in terms of primary cleavage of the carbon halogen bond to give α-carbonyl radicals (I) and/or cations (II). In the case of the 2,2-disubstituted compounds (1d-f), intermediates (II) undergo rearrangement with 1,2-shift of the phenyl or benzyl substituent prior to deprotonation. Minor by-products are the pentacyclic pyrone (4e) or 2-methylchromone (3a) (starting from 1e and 1f, respectively).