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

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

doi:10.1055/s-2003-44383

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 journal › Article › peer-review

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 language	English
Pages (from-to)	208-212
Number of pages	5
Journal	Synthesis
Volume	2004
Issue number	2
DOIs	https://doi.org/10.1055/s-2003-44383
Publication status	Published - Feb 2004

Keywords

ionic liquids
N-alkylation
phthalimide
heterocycle

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10.1055/s-2003-44383

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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.",

keywords = "ionic liquids, N-alkylation, phthalimide, heterocycle",

author = "Zhang-Gao Le and Zhen-Chu Chen and Yi Hu and Qinguo Zheng",

year = "2004",

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T1 - Organic reactions in ionic liquids: N-alkylation of phthalimide and several nitrogen heterocycles

AU - Le, Zhang-Gao

AU - Chen, Zhen-Chu

AU - Hu, Yi

AU - Zheng, Qinguo

PY - 2004/2

Y1 - 2004/2

N2 - 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.

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.

KW - ionic liquids

KW - N-alkylation

KW - phthalimide

KW - heterocycle

UR - https://www.thieme-connect.de/ejournals/abstract/synthesis/doi/10.1055/s-2003-44383

U2 - 10.1055/s-2003-44383

DO - 10.1055/s-2003-44383

M3 - Article

VL - 2004

SP - 208

EP - 212

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 2

ER -

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

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