Synthesis and isomerization of N-α-aza-heteroaryl-β-lactams

Autor:	Tullio Pilati, Catia Granito, Luigino Troisi, Emanuela Pindinelli, Alessandro Troisi, Ludovico Ronzini
Přispěvatelé:	Troisi, Luigino, Ronzini, Ludovico, Granito, Catia, Pindinelli, Emanuela, A., Troisi, T., Pilati
Rok vydání:	2006
Předmět:	Pyrimidinone Isomerization Allyl bromide Stereochemistry Organic Chemistry Ring (chemistry) Biochemistry Cycloaddition chemistry.chemical_compound Pyrimidinones chemistry Nitrogen atom Drug Discovery β lactams Carbonylative cycloaddition beta-Lactam
Zdroj:	Tetrahedron. 62:12064-12070
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.09.075
Popis:	The [2+2] carbonylative cycloaddition of N-alfa-aza-heteroaryl substituted imines with allyl bromide led partially to beta-lactams, which underwent isomerization to the more stable alfa,beta-unsaturated carbonyl compound. Pyrimidinone derivatives together with doubly unsaturated amides represent the remaining isolated products. The strong electron-withdrawing effect of the two alfa-aza-heterocycles linked to the nitrogen atom and to the C4 of the 2-azetidinone structure could give a ring expansion, through a 2-azetinone intermediate that affords the pyrimidinone compounds. The substituted amides, instead, should result from a ring-opening reaction of the beta-lactam.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c520bc641894aa7b8d885b201dfdd015 https://doi.org/10.1016/j.tet.2006.09.075 Zobrazit plný text záznamu Full Text from ScienceDirect