One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles

Wei Shun Hsu; Vijaykumar Paike; Chung-Ming Sun

doi:10.1007/s11030-013-9433-2

One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles

Wei Shun Hsu, Vijaykumar Paike, Chung-Ming Sun^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

An efficient strategy for the synthesis of pyrrolo[1,2- a ]-benzimidazole (PBI) linked to an ionic liquid (ILs) as a soluble support under microwave irradiation was explored. The key intermediate benzimidazoles were synthesized via N-acylation followed by cyclodehydration of IL-supported methyl-3-amino-4-(isobutylamino) benzoate. The synthesis of the IL-bound PBI was performed by one-pot three-component condensation under microwave dielectric heating, which involved a Knoevenagel condensation and a [4+1]-cycloaddition reaction. The reaction was monitored directly by means of ¹H NMR. All final products were obtained in good yield and high purity after precipitation. Graphic Abstract: [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	285-294
Number of pages	10
Journal	Molecular Diversity
Volume	17
Issue number	2
DOIs	https://doi.org/10.1007/s11030-013-9433-2
State	Published - 1 May 2013

Keywords

Ionic liquid
Microwave chemistry
Multicomponent reaction (MCR)
One-pot three component
Pyrrolo[1, 2-a]benzimidazole
Soluble supported synthesis

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title = "One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles",

abstract = "An efficient strategy for the synthesis of pyrrolo[1,2- a ]-benzimidazole (PBI) linked to an ionic liquid (ILs) as a soluble support under microwave irradiation was explored. The key intermediate benzimidazoles were synthesized via N-acylation followed by cyclodehydration of IL-supported methyl-3-amino-4-(isobutylamino) benzoate. The synthesis of the IL-bound PBI was performed by one-pot three-component condensation under microwave dielectric heating, which involved a Knoevenagel condensation and a [4+1]-cycloaddition reaction. The reaction was monitored directly by means of 1H NMR. All final products were obtained in good yield and high purity after precipitation. Graphic Abstract: [Figure not available: see fulltext.]",

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T1 - One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles

AU - Hsu, Wei Shun

AU - Paike, Vijaykumar

AU - Sun, Chung-Ming

PY - 2013/5/1

Y1 - 2013/5/1

N2 - An efficient strategy for the synthesis of pyrrolo[1,2- a ]-benzimidazole (PBI) linked to an ionic liquid (ILs) as a soluble support under microwave irradiation was explored. The key intermediate benzimidazoles were synthesized via N-acylation followed by cyclodehydration of IL-supported methyl-3-amino-4-(isobutylamino) benzoate. The synthesis of the IL-bound PBI was performed by one-pot three-component condensation under microwave dielectric heating, which involved a Knoevenagel condensation and a [4+1]-cycloaddition reaction. The reaction was monitored directly by means of 1H NMR. All final products were obtained in good yield and high purity after precipitation. Graphic Abstract: [Figure not available: see fulltext.]

AB - An efficient strategy for the synthesis of pyrrolo[1,2- a ]-benzimidazole (PBI) linked to an ionic liquid (ILs) as a soluble support under microwave irradiation was explored. The key intermediate benzimidazoles were synthesized via N-acylation followed by cyclodehydration of IL-supported methyl-3-amino-4-(isobutylamino) benzoate. The synthesis of the IL-bound PBI was performed by one-pot three-component condensation under microwave dielectric heating, which involved a Knoevenagel condensation and a [4+1]-cycloaddition reaction. The reaction was monitored directly by means of 1H NMR. All final products were obtained in good yield and high purity after precipitation. Graphic Abstract: [Figure not available: see fulltext.]

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KW - Microwave chemistry

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KW - Soluble supported synthesis

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