title: Reactions of 3-acylchromones with dimethyl 1,3-acetonedicarboxylate and 1,3-diphenylacetone: one-pot synthesis of functionalized 2-hydroxybenzophenones, 6H-benzo[c]chromenes and benzo[c]coumarins.
abstract: Reactions of 3-methoxalyl-, 3-polyfluoroacyl- and 3-aroylchromones with dimethyl 1,3-acetonedicarboxylate and 1,3-diphenylacetone in the presence of DBU proceed at the C-2 atom of the chromone system with pyrone ring-opening and subsequent formal [3 + 3] cyclocondensation to functionalized 2-hydroxybenzophenones, 6H-benzo[c]chromenes and benzo[c]coumarins, depending on the substituent at the 3-position. An NMR study and X-ray crystallographic analysis are reported. The compounds synthesized can be considered as promising scaffolds for the design of the novel UV-A/B and UV-B filters.
authors.affiliation: Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany. viktor.iaroshenko@uni-rostock.de
authors.forename: Viktor O
authors.initials: VO
authors.lastname: Iaroshenko
authors.forename: Iryna
authors.initials: I
authors.lastname: Savych
authors.forename: Alexander
authors.initials: A
authors.lastname: Villinger
authors.forename: Vyacheslav Ya
authors.initials: VY
authors.lastname: Sosnovskikh
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D007656:Ketoglutaric Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D001578:Benzopyrans; D003374:Coumarins; D007656:Ketoglutaric Acids; C524329:dimethyl 1,3-acetonedicarboxylate