ORGANIC SYNTHESES BASED ON 2-OXOGLUTARIC ACID .3. SYNTHESIS AND REACTIONS OF DIMETHYL (E)-2-OXOGLUTACONATE

Authors
BLITZKE T HARTENSTEIN H SICKER D WILDE H
Citation
T. Blitzke et al., ORGANIC SYNTHESES BASED ON 2-OXOGLUTARIC ACID .3. SYNTHESIS AND REACTIONS OF DIMETHYL (E)-2-OXOGLUTACONATE, Journal fur praktische Chemie, Chemiker-Zeitung, 335(8), 1993, pp. 683-686
Citations number
13
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
335
Issue
8
Year of publication
1993
Pages
683 - 686
Database
ISI
SICI code
0941-1216(1993)335:8<683:OSBO2A>2.0.ZU;2-T
Abstract
Dimethyl (E)-2-oxoglutaconate 1 obtained by dehydrobromination of dime thyl 3-bromo-2-oxoglutarate reacts with o-phenylendiamine to form the quinoxalin-2(1H)-one 2, and with phenylhydrazine to yield the 4,5-dihy dropyrazole 3. Furthermore, a Doebner-von Miller-type reaction affords the 8-carboxy quinoline derivative 4. Finally, addition of bromine le ads diastereoselectively to the racemate of dimethyl 3S,4R- and 3R,4S- dibromo-2-oxoglutarate 5.