Organic reactions in ionic liquids: N-alkylation of phthalimide and several nitrogen heterocycles

Zhang-Gao Le, Zhen-Chu Chen, Yi Hu, Qinguo Zheng

Research output: Contribution to journalArticle

Abstract

N-Alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in ionic liquids ([bmim]BF4 = 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim]PF6 = 1-butyl-3-methylimida-zolium hexafluorophosphate, [buPy]BF4 = butylpyridinium tetra­fluoroborate) in the presence of potassium hydroxide as a base. In this manner, phthalimide, indole, benzimidazole, succinimide can be successfully alkylated. The procedure is convenient, efficient, and generally affords the N-alkylated product exclusively.
Original languageEnglish
Pages (from-to)208-212
Number of pages5
JournalSynthesis
Volume2004
Issue number2
DOIs
Publication statusPublished - Feb 2004

Fingerprint

Bearings (structural)
Ionic Liquids
Potassium hydroxide
Alkylation
Ionic liquids
Nitrogen
Heterocyclic Compounds
Atoms
Hydrogen
phthalimide
1-butyl-3-methylimidazolium tetrafluoroborate

Keywords

  • ionic liquids
  • N-alkylation
  • phthalimide
  • heterocycle

Cite this

Le, Zhang-Gao ; Chen, Zhen-Chu ; Hu, Yi ; Zheng, Qinguo. / Organic reactions in ionic liquids: N-alkylation of phthalimide and several nitrogen heterocycles. In: Synthesis. 2004 ; Vol. 2004, No. 2. pp. 208-212.
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Organic reactions in ionic liquids: N-alkylation of phthalimide and several nitrogen heterocycles. / Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qinguo.

In: Synthesis, Vol. 2004, No. 2, 02.2004, p. 208-212.

Research output: Contribution to journalArticle

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AB - N-Alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in ionic liquids ([bmim]BF4 = 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim]PF6 = 1-butyl-3-methylimida-zolium hexafluorophosphate, [buPy]BF4 = butylpyridinium tetra­fluoroborate) in the presence of potassium hydroxide as a base. In this manner, phthalimide, indole, benzimidazole, succinimide can be successfully alkylated. The procedure is convenient, efficient, and generally affords the N-alkylated product exclusively.

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