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Novel (E)- and (Z)-2-styrylchromones from (E,E)-2'-hydroxycinnamylideneacetophenones - Xanthones from daylight photooxidative cyclization of (E)-2-styrylchromones

AuthorsSilva, Artur M. S.; Pinto, Diana C. G. A.; Tavares, Hilario R.; Cavaleiro, José A. S; Jimeno, M. Luisa; Elguero, José
(E)-and (Z)-2-Styrylchromones
Oxidative cyclizations
Configuration determination
Issue Date1998
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry 9 : 2031-2038 (1998)
AbstractThe oxidative cyclization of (E,E)-29-hydroxycinnamyl- obtained. The stereochemistry of the (E,E)-cinnamylidene- ideneacetophenones 1a–e, and (E,E)-29-benzyloxy-69- acetophenones 1 and (E)-and (Z)-2-styrylchromones 3 and 4 hydroxycinnamylideneacetophenones 1i–l with DMSO/ was established by NOE experiments. The induced daylight iodine, gave (E)-2-styrylchromones 3a–e,i–l. However, in the photooxidative cyclization of some (E)-2-styrylchromones case of (E,E)-ã-alkyl-29-hydroxycinnamylideneacetophen- 3a,f–h gave 12H-benzo[a]xanthene-12-ones 6a,f–h. ones 1f–h,(E)-and (Z)-2-styrylchromones 3f–h and 4f–h were
Publisher version (URL)http://bit.ly/jEsJqg
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