Acetals and vinyl ethers of unsaturated aldehydes and ketones in the new syntheses of heterocyclic compounds: XII. New alternatives of acid condensation of cyclohexane-1,4-diones with hydroxyarylaldehydes under dehydration conditions. Fluorecence spectra of the products

Citation
Ep. Olekhnovich et al., Acetals and vinyl ethers of unsaturated aldehydes and ketones in the new syntheses of heterocyclic compounds: XII. New alternatives of acid condensation of cyclohexane-1,4-diones with hydroxyarylaldehydes under dehydration conditions. Fluorecence spectra of the products, RUSS J ORG, 37(4), 2001, pp. 527-538
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
10704280 → ACNP
Volume
37
Issue
4
Year of publication
2001
Pages
527 - 538
Database
ISI
SICI code
1070-4280(200104)37:4<527:AAVEOU>2.0.ZU;2-X
Abstract
1,3-Diethoxy-2-R-5,5-R-1,R-1-1-cyclohexenylium perchlorates in condensation with 2-hydroxyaryl-aldehydes under dehydration conditions give rise to 3-e thoxy-1,2-dihydroxanthylium perchlorates that with the second molecule of 2 -hydroxyarylaldehyde afford 13H-chromeno[3,2-b]xanth-5-ylium perchlorates, and with primary and secondary amines yield 3-(R-2,R-3-amino)-1,2-dihydroxa nthylium perchlorates. The condensation of 2-bromodimedone with salicylalde hydes in triethyl orthoformate and perchloric acid medium furnished 6-bromo -13,13-dimethyl-13H-chromeno[3,2-b]xanth-5-ylium perchlorates. The latter c ompounds show strong fluorescence in 530-630 nm region with 0.48-0.98 quant um efficiency. Under similar conditions the dimedone and 2-acetyldimedone a fford with 2-hydroxyarylaldehydes tris-condensation products: 2,10-dimethox y-6-(3-methoxy-6-oxo-2,4-cyclohexadienylidenemethyl)-7,7-dimethyl-7H-chrome no[2,3-a]-xanth-13-ylium perchlorate and 2,10-dimethoxy-6-(6-methoxychromyl ium-2-yl)-13,13-dimethyl-13H-chromeno[3,2-b]xanth-5-ylium diperchlorate res pectively.