REACTION OF DIANIONS OF ACYCLIC BETA-ENAMINO KETONES WITH ELECTROPHILES .7. SYNTHESIS OF 5-(MONOALKYLAMINO)-3-OXO GAMMA,DELTA-UNSATURATED ACIDS AND ESTERS AND OF 3-(MONOALKYLAMINO)-5-OXO BETA,GAMMA-UNSATURATEDESTERS

Authors
BARTOLI G BOSCO M GUERRIERI A DALPOZZO R DENINO A IANTORNO E PALMIERI G
Citation
G. Bartoli et al., REACTION OF DIANIONS OF ACYCLIC BETA-ENAMINO KETONES WITH ELECTROPHILES .7. SYNTHESIS OF 5-(MONOALKYLAMINO)-3-OXO GAMMA,DELTA-UNSATURATED ACIDS AND ESTERS AND OF 3-(MONOALKYLAMINO)-5-OXO BETA,GAMMA-UNSATURATEDESTERS, Gazzetta chimica italiana, 126(1), 1996, pp. 25-29
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Gazzetta chimica italiana → ACNP
ISSN journal
00165603
Volume
126
Issue
1
Year of publication
1996
Pages
25 - 29
Database
ISI
SICI code
0016-5603(1996)126:1<25:RODOAB>2.0.ZU;2-W
Abstract
Dianions of beta-(monoalkylamino) alpha,beta-unsaturated ketones react with carbon dioxide and diethyl carbonate leading to the title compou nds. 2-alkyl-5-(monoalkylamino)-3-oxo gamma,delta-unsaturated acids ar e unstable and decarboxylate in a few hours after isolation. 3-(monoal kylamino)-5-oxo beta,gamma-unsaturated acids are never recovered from gamma-dianions. Transmetallation from enaminone dianion to esters may occur. gamma-Dianions require a non-nucleophilic base to obtain better results.