A Highly Efficient and Eco-Friendly Synthesis of Disubstituted Imidazoles in Ionic Liquid from Gem-Dibromo Vinylarenes and Amidines

Puneet Kumar Gupta; Maged A. Azzam; Mohammad Saquib; Mohd Kamil Hussain

doi:10.1080/10406638.2022.2061532

A Highly Efficient and Eco-Friendly Synthesis of Disubstituted Imidazoles in Ionic Liquid from Gem-Dibromo Vinylarenes and Amidines

Puneet Kumar Gupta
, Maged A. Azzam
, Mohammad Saquib
, Mohd Kamil Hussain

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

13 Scopus citations

Abstract

A rapid and versatile, transition metal free, green methodology for the synthesis of 2,5-disubstituted-1H-imidazoles, using gem-dibromo vinylarenes and amidines is described. The disclosed strategy utilizes a combination of the easily available and nontoxic, naturally occurring mild base, NaHCO₃ and the ionic liquid, 1-butyl-3-methyl imidazolium tetrafluoroborate [bmim][BF₄], for promoting the successive aminations through intermolecular C(sp²)-N and intramolecular C(sp²)-N bonds formation to furnish diverse disubstituted imidazole derivatives.

Original language	English
Pages (from-to)	3089-3098
Number of pages	10
Journal	Polycyclic Aromatic Compounds
Volume	43
Issue number	4
DOIs	https://doi.org/10.1080/10406638.2022.2061532
State	Published - 2023
Externally published	Yes

Keywords

2,5-diaryl-1H-imidazoles
amidines
gem-dibromo vinylarenes
ionic liquids

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10.1080/10406638.2022.2061532

Cite this

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title = "A Highly Efficient and Eco-Friendly Synthesis of Disubstituted Imidazoles in Ionic Liquid from Gem-Dibromo Vinylarenes and Amidines",

abstract = "A rapid and versatile, transition metal free, green methodology for the synthesis of 2,5-disubstituted-1H-imidazoles, using gem-dibromo vinylarenes and amidines is described. The disclosed strategy utilizes a combination of the easily available and nontoxic, naturally occurring mild base, NaHCO3 and the ionic liquid, 1-butyl-3-methyl imidazolium tetrafluoroborate [bmim][BF4], for promoting the successive aminations through intermolecular C(sp2)-N and intramolecular C(sp2)-N bonds formation to furnish diverse disubstituted imidazole derivatives.",

keywords = "2,5-diaryl-1H-imidazoles, amidines, gem-dibromo vinylarenes, ionic liquids",

author = "Gupta, \{Puneet Kumar\} and Azzam, \{Maged A.\} and Mohammad Saquib and Hussain, \{Mohd Kamil\}",

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year = "2023",

doi = "10.1080/10406638.2022.2061532",

language = "English",

volume = "43",

pages = "3089--3098",

journal = "Polycyclic Aromatic Compounds",

issn = "1040-6638",

publisher = "Taylor and Francis Ltd.",

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}

TY - JOUR

T1 - A Highly Efficient and Eco-Friendly Synthesis of Disubstituted Imidazoles in Ionic Liquid from Gem-Dibromo Vinylarenes and Amidines

AU - Gupta, Puneet Kumar

AU - Azzam, Maged A.

AU - Saquib, Mohammad

AU - Hussain, Mohd Kamil

PY - 2023

Y1 - 2023

N2 - A rapid and versatile, transition metal free, green methodology for the synthesis of 2,5-disubstituted-1H-imidazoles, using gem-dibromo vinylarenes and amidines is described. The disclosed strategy utilizes a combination of the easily available and nontoxic, naturally occurring mild base, NaHCO3 and the ionic liquid, 1-butyl-3-methyl imidazolium tetrafluoroborate [bmim][BF4], for promoting the successive aminations through intermolecular C(sp2)-N and intramolecular C(sp2)-N bonds formation to furnish diverse disubstituted imidazole derivatives.

AB - A rapid and versatile, transition metal free, green methodology for the synthesis of 2,5-disubstituted-1H-imidazoles, using gem-dibromo vinylarenes and amidines is described. The disclosed strategy utilizes a combination of the easily available and nontoxic, naturally occurring mild base, NaHCO3 and the ionic liquid, 1-butyl-3-methyl imidazolium tetrafluoroborate [bmim][BF4], for promoting the successive aminations through intermolecular C(sp2)-N and intramolecular C(sp2)-N bonds formation to furnish diverse disubstituted imidazole derivatives.

KW - 2,5-diaryl-1H-imidazoles

KW - amidines

KW - gem-dibromo vinylarenes

KW - ionic liquids

UR - https://www.scopus.com/pages/publications/85129338727

U2 - 10.1080/10406638.2022.2061532

DO - 10.1080/10406638.2022.2061532

M3 - Article

AN - SCOPUS:85129338727

SN - 1040-6638

VL - 43

SP - 3089

EP - 3098

JO - Polycyclic Aromatic Compounds

JF - Polycyclic Aromatic Compounds

IS - 4

ER -

A Highly Efficient and Eco-Friendly Synthesis of Disubstituted Imidazoles in Ionic Liquid from Gem-Dibromo Vinylarenes and Amidines

Abstract

Keywords

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