STEREOSELECTIVE SYNTHESIS OF N,N'-DIARYL-2,5-DIOXOPIPERAZINES FROM HOMOCHIRAL OR RACEMIC 2-BROMOPROPANANILIDES

Authors
DANGELI F MARCHETTI P RONDANIN R BERTOLASI V
Citation
F. Dangeli et al., STEREOSELECTIVE SYNTHESIS OF N,N'-DIARYL-2,5-DIOXOPIPERAZINES FROM HOMOCHIRAL OR RACEMIC 2-BROMOPROPANANILIDES, Journal of organic chemistry, 61(4), 1996, pp. 1252-1255
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
4
Year of publication
1996
Pages
1252 - 1255
Database
ISI
SICI code
0022-3263(1996)61:4<1252:SSONFH>2.0.ZU;2-5
Abstract
N,N'-Diaryl-2,5-dioxopiperazines 8 and 9, related to the amino acid al anine, are easily obtained by self-cyclocoupling of 2-bromopropananili des 7. The cis-(R,R) or cis-(S,S)/trans-(R,S) distribution is controll ed, to varying extents, by starting either from a single enantiomer or racemate and by the promoter, aryl substituent, and solvent. H-1 NMR spectra of the members of six diastereomeric couples and X-ray structu res of representative products are reported.