REARRANGEMENT AND AROMATIZATION OF THE KETOENAMINE ADDUCTS FROM DIBENZOYLDIAZENE AND SECONDARY ALPHA-KETOENAMINES AND BETA-KETOENAMINES

Authors
FELLUGA F NITTI P PIZZIOLI A PRODAN M RUSSO C
Citation
F. Felluga et al., REARRANGEMENT AND AROMATIZATION OF THE KETOENAMINE ADDUCTS FROM DIBENZOYLDIAZENE AND SECONDARY ALPHA-KETOENAMINES AND BETA-KETOENAMINES, Gazzetta chimica italiana, 127(1), 1997, pp. 31-35
Citations number
16
Categorie Soggetti
Chemistry
Journal title
Gazzetta chimica italiana → ACNP
ISSN journal
00165603
Volume
127
Issue
1
Year of publication
1997
Pages
31 - 35
Database
ISI
SICI code
0016-5603(1997)127:1<31:RAAOTK>2.0.ZU;2-Q
Abstract
The reaction of secondary alpha-ketoenamines 10 with dibenzoyldiazene (DBD) furnish exclusively the corresponding enamine type adducts 11, w hich rearrange at 80 degrees C in acidic medium to the more stable ena minone isomers 12. Secondary beta-ketoenamines 14 react with the same electrophilic diazene only at 80 degrees C to give the open-chain addu cts 15, which undergo aromatization under prolonged heating to the phe nol derivatives 16. The presence of 1,3,4-oxadiazine derivatives could not be observed.