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Titolo:
Stereoisomerism in 3-[N-(2-acetoxypropanoyl)-N-acylamino]quinazolin-4(3H)-ones, enantioselective acylating agents
Autore:
Al-Sehemi, AG; Atkinson, RS; Fawcett, J; Russell, DR;
Indirizzi:
Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England Univ Leicester Leicester Leics England LE1 7RH er LE1 7RH, Leics, England
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 24, , anno: 2000,
pagine: 4413 - 4421
SICI:
1472-7781(2000):24<4413:SI3>2.0.ZU;2-Q
Fonte:
ISI
Lingua:
ENG
Soggetto:
N-N BOND; CHIRAL AXIS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
10
Recensione:
Indirizzi per estratti:
Indirizzo: Atkinson, RS Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England Univ Leicester Leicester Leics England LE1 7RH eics, England
Citazione:
A.G. Al-Sehemi et al., "Stereoisomerism in 3-[N-(2-acetoxypropanoyl)-N-acylamino]quinazolin-4(3H)-ones, enantioselective acylating agents", J CHEM S P1, (24), 2000, pp. 4413-4421

Abstract

The title compounds diacylaminoquinazolinones (DAQs) are enantioselective acylation agents for amines and a detailed study of their stereostructures was undertaken with the aim of understanding how this enantioselectivity arises. The N-N bond in these DAQs is a chiral axis. Even where both N-acyl groups are (S)-2-acetoxypropanoyl, the N-N bond is still a chiral axis because in the most stable conformation of the planar imide moiety, one exo/endoorientation of the carbonyl groups is much preferred over the alternative (endo/exo) as revealed by NMR spectroscopy. A conformational preference within the 2-acetoxypropanoyl grouping accounts for the presence of a single exo/endo conformation in solution for some of these DAQs (see above) but an interconverting exo/endo reversible arrow endo/exo mixture for others. Where a single exo/endo conformation is present in solution, evidence is presented that this closely resembles the X-ray determined crystal structure. A mechanism for the second acylation step to form these DAQs is proposed, which involves preliminary O-acylation of the 3-(monoacylamino)quinazolinone.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/04/20 alle ore 18:39:06