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

Research output: Contribution to journalArticlepeer-review

7 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 languageEnglish (US)
Pages (from-to)5874-5877
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number43
DOIs
StatePublished - 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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