N- and C-Acylation in β-Enamino Ketones: Structural Effects on Regiocontrol

Autor:	Marcelo Rossatto, Pâmela S. Vargas, Pablo Machado, Fernanda A. Rosa, Marcos A. P. Martins, Helio G. Bonacorso, Nilo Zanatta
Rok vydání:	2007
Předmět:	Acylation chemistry.chemical_compound chemistry Oxalyl chloride Organic Chemistry Pyridine Regioselectivity Trifluoroacetic anhydride Medicinal chemistry
Zdroj:	Synlett. 2007:3165-3171
ISSN:	1437-2096 0936-5214
Popis:	The acylation reaction of secondary (R 1 = H) β-enamino ketones [RCOCH=CHNR 1 R 2 , where R = CF 3 , CCl 3 , Ph, 4-FC 6 H 4 , 4-NO 2 C 6 H 4 , thien-2-yl; R 1 = H, Me; R 2 = Me, Bn, Ph, 4-NO 2 C 6 H 4 ] with trifluoroacetic anhydride or ethyl oxalyl chloride in pyridine led regiospecifically to a series of 14 N-acylated enaminones in good yields (72-88%). On the other hand, when tertiary enaminones (R 1 , R 2 = Me) were used, the acylation reaction led to a series of 12 C-acylated enaminones in good to excellent yields (75-92%).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9afab046dc96870473c597f1336ae76c https://doi.org/10.1055/s-2007-992382 Zobrazit plný text záznamu