Literature DB >> 26663985

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 Gu1, Gunda I Georg2.   

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.

Entities:  

Keywords:  2,3-dihydro-4-pyridones; 4-(pyrrolidin-1-yl)furan-2(5H)-one; Mannich reaction; regioselective alkylation

Year:  2015        PMID： 26663985      PMCID： PMC4671294          DOI： 10.1016/j.tetlet.2015.09.004

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

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Journal:  Cell Cycle       Date:  2005-09-06       Impact factor: 4.534

2.  Synthesis and reactivity of N-acyl-5- (1-hydroxyalkyl)-2,3-dihydro-4-pyridones.

Authors:  D L Comins; A C Hiebel; S Huang
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

3.  Synthesis of tylocrebrine and related phenanthroindolizidines by VOF3-mediated oxidative aryl-alkene coupling.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  Org Lett       Date:  2010-12-14       Impact factor: 6.005

4.  Tautomeric switching and metal-cation sensing of ligand-equipped 4-hydroxy-/4-oxo-1,4-dihydroquinolines.

Authors:  Aleksandar R Todorov; Martin Nieger; Juho Helaja
Journal:  Chemistry       Date:  2012-04-19       Impact factor: 5.236

5.  Total Syntheses and Cytotoxicity of (R)- and (S)-Boehmeriasin A.

Authors:  Matthew W Leighty; Gunda I Georg
Journal:  ACS Med Chem Lett       Date:  2011-04-14       Impact factor: 4.345

6.  Palladium(II)-catalyzed dehydrogenative alkenylation of cyclic enaminones via the Fujiwara-Moritani reaction.

Authors:  Yi-Yun Yu; Micah J Niphakis; Gunda I Georg
Journal:  Org Lett       Date:  2011-10-13       Impact factor: 6.005

7.  Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

Authors:  Yi-Yun Yu; Lei Bi; Gunda I Georg
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

8.  Copper-assisted palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids.

Authors:  Yong Wook Kim; Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2012-10-22       Impact factor: 4.354

9.  Palladium(II)-catalyzed direct arylation of enaminones using organotrifluoroborates.

Authors:  Haibo Ge; Micah J Niphakis; Gunda I Georg
Journal:  J Am Chem Soc       Date:  2008-03-06       Impact factor: 15.419

10.  Cross-couplings of unactivated secondary alkyl halides: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides.

Authors:  Jianrong Steve Zhou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419
  10 in total

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