Reactions of .ALPHA.-alkyl- and .ALPHA.-aryl-substituted N-benzylideneamines with trihaloacetylating agents

Autor:	Toshiaki Morimoto, Minoru Sekiya
Rok vydání:	1977
Předmět:	chemistry.chemical_classification Hydrogen Aryl Quinoline Xylene chemistry.chemical_element General Chemistry General Medicine Acylation chemistry.chemical_compound chemistry Drug Discovery Trichloroacetyl chloride Organic chemistry Trifluoroacetic anhydride Alkyl
Zdroj:	Chemical and Pharmaceutical Bulletin. 25:1230-1236
ISSN:	1347-5223 0009-2363
Popis:	Reactions of imines with trichloroacetylating agents rely upon their structural differences. 3, 3-Dichloro-2-azetidinone formation was effected by the reaction of α-arylsubstituted N-benzylideneamines similarly to that of N-benzylideneamines. The imines, of which imino carbons are bound to alkyls possessing at least one hydrogen at C1 of the alkyls, however, reacted with trichloroacetic anhydride and trichloroacetyl chloride to give β-trichloroacetylated enamines. In the reaction with trifluoroacetic anhydride in place of trichloroacetic anhydride N-trifluoroacetylenamines were obtained instead, but the products easily undergo N→C migration on heating in xylene to give β-trifluoroacetylated enamines. Acid-catalyzed quinoline ring-closures of the β-trihaloacetylated enamines obtained above are also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f670ac1a07b9a422f5936dcd72a40f94 https://doi.org/10.1248/cpb.25.1230 Zobrazit plný text záznamu