Regioselective C5-alkylation and C5-methylcarbamate formation of 2,3-dihydro-4-pyridones and C3-alkylation and C3-methylcarbamate formation of 4-(pyrrolidin-1-yl)furan-2(5H)-one

Regioselective C5-alkylation and C5-methylcarbamate formation of 2,3-dihydro-4-pyridones and C3-alkylation and C3-methylcarbamate formation of 4-(pyrrolidin-1-yl)furan-2(5H)-one

[Display omitted] Reactions of N-alkyl-2,3-dihydro-4-pyridones and 4-(pyrrolidin-1-yl)furan-2(5H)-one with aldehydes and triethylsilane in a one-flask procedure provided C5 and C3 alkylated derivatives, respectively. Mannich-type reactions with formaldehyde and carbamates in the presence of lithium...

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Veröffentlicht in:Tetrahedron letters 2015-10, Vol.56 (43), p.5874-5877
Hauptverfasser: Gu, Xingxian, Georg, Gunda I.
Format: Artikel
Sprache:eng
Schlagworte:
2,3-Dihydro-4-pyridones
4-(Pyrrolidin-1-yl)furan-2(5H)-one
Mannich reaction
Regioselective alkylation
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Zusammenfassung:[Display omitted] Reactions of N-alkyl-2,3-dihydro-4-pyridones and 4-(pyrrolidin-1-yl)furan-2(5H)-one with aldehydes and triethylsilane in a one-flask procedure provided C5 and C3 alkylated derivatives, respectively. Mannich-type reactions with formaldehyde and carbamates in the presence of lithium perchlorate furnished C5/C3 methylcarbamates.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.09.004