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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 25, Number 6
BKCSDE 25(6)
June 20, 2004 

Synthesis of a New Diels-Alder Quinone Adduct and Its Use in Preparing Thiazolo- and Oxazoloquinolines
A. S. Hammam, M. S. K. Youssef*, Sh. M. Radwan, M. A. Abdel-Rahman
Cinnamaldehydeoxime, Bromanil, Monoadduct, Thiazoloquinolines, Oxazoloquinolines
Syn (or anti) cinnamaldehydeoxime (1a, b) undergoes Diels-Alder addition to tetrabromo-p-benzoquinone (2) in dry xylene in 1 : 1 and 2 : 1 molar ratios to give the mono- and diadducts 3 and 4a, b respectively. The reaction of 3 with thioamides in ethanol gave thiazoloquinoline diones 6a-d, whereas with acid amides in ethylene glycol, it gave oxazoloquinolinediones 12a-f.
779 - 785
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