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

Bibliographical note

Funding Information:
We gratefully acknowledge financial support from the National Institutes of Health Grant GM081267 and the University of Minnesota through the Vince and McKnight Endowed Chairs. We thank Erick Carlson for his assistance with the assembly of the supplementary data.

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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10.1016/j.tetlet.2015.09.004

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@article{7115a37eb45541fd960799cbe2897d6f,

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 = "Funding Information: We gratefully acknowledge financial support from the National Institutes of Health Grant GM081267 and the University of Minnesota through the Vince and McKnight Endowed Chairs. We thank Erick Carlson for his assistance with the assembly of the supplementary data. Publisher Copyright: {\textcopyright} 2015 The Authors.",

year = "2015",

month = oct,

day = "21",

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

language = "English (US)",

volume = "56",

pages = "5874--5877",

journal = "Tetrahedron Letters",

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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.

N1 - Funding Information: We gratefully acknowledge financial support from the National Institutes of Health Grant GM081267 and the University of Minnesota through the Vince and McKnight Endowed Chairs. We thank Erick Carlson for his assistance with the assembly of the supplementary data. Publisher Copyright: © 2015 The Authors.

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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U2 - 10.1016/j.tetlet.2015.09.004

DO - 10.1016/j.tetlet.2015.09.004

M3 - Article

C2 - 26663985

AN - SCOPUS:84945460314

SN - 0040-4039

VL - 56

SP - 5874

EP - 5877

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

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

Bibliographical note

Keywords

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