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

Xingxian Gu; Gunda I. Georg

doi:10.1016/j.tetlet.2015.09.004

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

Xingxian Gu, Gunda I. Georg

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	5874-5877
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2015.09.004
State	Published - Oct 21 2015

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Publisher Copyright:
© 2015 The Authors.

Keywords

2,3-Dihydro-4-pyridones
4-(Pyrrolidin-1-yl)furan-2(5H)-one
Mannich reaction
Regioselective alkylation

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title = "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",

abstract = "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.",

keywords = "2,3-Dihydro-4-pyridones, 4-(Pyrrolidin-1-yl)furan-2(5H)-one, Mannich reaction, Regioselective alkylation",

author = "Xingxian Gu and Georg, {Gunda I.}",

note = "Publisher Copyright: {\textcopyright} 2015 The Authors.",

year = "2015",

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doi = "10.1016/j.tetlet.2015.09.004",

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T1 - 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

AU - Gu, Xingxian

AU - Georg, Gunda I.

PY - 2015/10/21

Y1 - 2015/10/21

N2 - 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.

AB - 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.

KW - 2,3-Dihydro-4-pyridones

KW - 4-(Pyrrolidin-1-yl)furan-2(5H)-one

KW - Mannich reaction

KW - Regioselective alkylation

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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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

Abstract

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