Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
Reactions of methyl 2-aryl-2H-azirine-3-carboxylates with nucleophiles
Autore:
Alves, MJ; Gilchrist, TL; Sousa, JH;
Indirizzi:
Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England Univ Liverpool Liverpool Merseyside England L69 7ZD , Merseyside, England Univ Minho, Dept Quim, P-4710 Braga, Portugal Univ Minho Braga Portugal P-4710 inho, Dept Quim, P-4710 Braga, Portugal
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 10, , anno: 1999,
pagine: 1305 - 1310
SICI:
0300-922X(19990521):10<1305:ROM2WN>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
HETEROCYCLIC SYNTHESIS; VINYL AZIDES; PHOTOCHEMICAL DECOMPOSITION; SUBSTITUENTS; 2H-AZIRINES; BOND;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
25
Recensione:
Indirizzi per estratti:
Indirizzo: Gilchrist, TL Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England Univ Liverpool Liverpool Merseyside England L69 7ZD England
Citazione:
M.J. Alves et al., "Reactions of methyl 2-aryl-2H-azirine-3-carboxylates with nucleophiles", J CHEM S P1, (10), 1999, pp. 1305-1310

Abstract

Reactions of the methyl 2-aryl-2H-azirine-3-carboxylates 1a and 1b with nucleophiles are described. Thiols add to the C=N bond to give aziridines 4-6. Propargyl alcohol similarly gives the aziridine 7. Primary and secondary aliphatic amines react with the azirines to give methyl 3-aminoacrylates 8-12. 4-Cyclohexen-1-ylmorpholine and 1-cyclopenten-1-ylpyrrolidine react with the azirine 1a to give products formulated as the aziridine 13 and the vinylidenecyclopentanone 14, respectively, in contrast to previously reportedreactions of enamines with azirines from which pyrroles were isolated, Acetylacetone gives a pyrrole-3-carboxylate 15 in low yield with the azirine 1a. All these products have been rationalised by invoking initial addition of the nucleophile to the C=N bond of the azirine. The tetrahydrofuran-2-yl radical also adds to the C=N bond of the azirine la, giving the aziridine 16 as a single diastereoisomer. X-Ray crystal structures of methyl (E)-3-amino-3-(2,6-dichlorophenyl)-2-morpholin-4-ylpropenoate 8 and of methyl 3-(2,6-dichlorophenyl)-2-(tetrahydrofuran-2-yl)aziridine-2-carboxylate 16 are reported.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/09/20 alle ore 21:41:04