Nucleophilic addition to 3‐methyl‐1‐(4‐nitrophenyl)‐2‐phenyl‐4,5‐dihydroimidazolium iodide

doi:10.1002/JHET.5570370552

Paper

Nucleophilic addition to 3‐methyl‐1‐(4‐nitrophenyl)‐2‐phenyl‐4,5‐dihydroimidazolium iodide

Published Sep 1, 2000 · Chizhong Xia, Yi-Xin Tang, P. Zhou

Journal of Heterocyclic Chemistry

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Abstract

Reactions of the 1,2-diaryl 4,5-dihydroimidazolium, represented by 3-methyl-1-(4-nitrophenyl)-2-phenyl-4,5-dihydroimidazolium iodide 1, with ethylenediamine afforded a benzylidyne unit transferred product, 2-phenyl-2-imidazoline 2; a ring-opened adduct 4 was produced when excess ethylenediamine was used. Reactions of 1 with hydroxylamine, malononitrile, and nitromethane anions produced ring-opened products, 5, 7, and 8 respectively.

Study Snapshot

This study demonstrates that 3-methyl-1-(4-nitrophenyl)-2-phenyl-4,5-dihydroimidazolium iodide can be converted into benzylidyyne units by nucleophilic addition to ethylenediamine, malononitrile

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Nucleophilic addition to 3‐methyl‐1‐(4‐nitrophenyl)‐2‐phenyl‐4,5‐dihydroimidazolium iodide

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References

Nucleophilic addition to substituted 1 H -4,5-dihydroimidazolium salts

Substituted 1H-4,5-dihydroimidazolium salts readily react with nucleophilic reagents, forming stable or acyclic compounds maintaining the structural ethylenediamine unit.

Providing One-Carbon Units for Biological Methylations: Mechanistic Studies on Serine Hydroxymethyltransferase, Methylenetetrahydrofolate Reductase, and Methyltetrahydrofolate-Homocysteine Methyltransferase

Methyltetrahydrofolate-Homocysteine Methyltransferase plays a crucial role in biological methylation reactions, providing one-carbon units for biological methylation reactions.

Reaction of an asymmetric imidazolinium compound with nucleophiles

Asymmetric imidazolinium compounds react easily with nucleophiles to produce various stable addition products, including N-benzoyl-N-methyl-N′-(p-nitrophenyl)ethylenediamine (4).

Reactions of S-alkyl NN-disubstituted thioamide salts. Part 2. Orthothioamide derivatives

NN-disubstituted thioamide salts react with potassium cyanide to produce quaternary cyanides, which can be further converted into cyano-amides via aminomalononitriles.

Citations

N-Pyridinium imidates as new sources of 2-aminoimidazole and imidazoline derivatives

N-pyridinium imidates can be used to create new 2-aminoimidazole and imidazoline derivatives through a three-step process.

1,2‐Dimethyl‐3‐(2‐nitrophenyl)‐4,5‐dihydroimidazolium iodide

The crystal structure of 1,2Dimethyl-3(2nitro-phenyl)4,5dihydro-imidazolium iodide reveals a three-dimensional structure with intermolecular C-HO and C-HI hydrogen bonds.

REACTIONS OF 2,3-DIARYL-1-METHYL-4,5-DIHYDROIMIDAZOLIUM IODIDES WITH NUCLEOPHILIC REAGENTS

2,3-Diaryl imidazolium salts can be used to produce various products with one-carbon unit transfer, mimicking the one-carbon unit transfer function for tetrahydrofolate coenzymes.

AMINOLYSIS OF 1,2-DIMETHYL- 3-ARYLSULFONYL-4,5-DIHYDROIMIDAZOLIUM IODIDES WITH AROMATIC AMINES

This study demonstrates that arylsulfonylimidazolium salts can produce N′-aryl-N-methyl-N-(2-arylsulfonylamino)ethylacetamidine monohydroiodides in good to excellent yields through nu

NUCLEOPHILIC ADDITION TO 1,2-DIMETHYL-3-ARYLSULFONYL- 4,5-DIHYDROIMIDAZOLIUM IODIDES

This study demonstrates the high yield and excellent product formation of benzenesulfonamide derivatives from arylsulfonylimidazolium iodides with malononitrile or nitromethane anions.

A CONVENIENT SYNTHESIS OF IMIDAZOLIUM SALTS AND TRISUBSTITUTED ETHYLENEDIAMINE DERIVATIVES

This study demonstrates a convenient method for preparing imidazolium salts and trisubstituted ethylenediamine derivatives from commercially available 2-methyl-2-imidazoline, yielding high-yield products.

Ring-opening reactions of 2-imidazolines and their applications

2-imidazoline moiety's chemical instability enables diverse scaffold-generating and scaffold-morphing transformations under various conditions, expanding its applications in organic chemistry.

4.02 – Imidazoles

Imidazole chemistry has advanced significantly since 1995, with significant advances in reactivity, synthesis, and applications.

Nucleophilic addition to 3‐methyl‐1‐(4‐nitrophenyl)‐2‐phenyl‐4,5‐dihydroimidazolium iodide

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References

Nucleophilic addition to substituted 1 H -4,5-dihydroimidazolium salts

Substituted 1H-4,5-dihydroimidazolium salts readily react with nucleophilic reagents, forming stable or acyclic compounds maintaining the structural ethylenediamine unit.

Providing One-Carbon Units for Biological Methylations: Mechanistic Studies on Serine Hydroxymethyltransferase, Methylenetetrahydrofolate Reductase, and Methyltetrahydrofolate-Homocysteine Methyltransferase

Methyltetrahydrofolate-Homocysteine Methyltransferase plays a crucial role in biological methylation reactions, providing one-carbon units for biological methylation reactions.

Reaction of an asymmetric imidazolinium compound with nucleophiles

Asymmetric imidazolinium compounds react easily with nucleophiles to produce various stable addition products, including N-benzoyl-N-methyl-N′-(p-nitrophenyl)ethylenediamine (4).

Reactions of S-alkyl NN-disubstituted thioamide salts. Part 2. Orthothioamide derivatives

NN-disubstituted thioamide salts react with potassium cyanide to produce quaternary cyanides, which can be further converted into cyano-amides via aminomalononitriles.

Citations

N-Pyridinium imidates as new sources of 2-aminoimidazole and imidazoline derivatives

N-pyridinium imidates can be used to create new 2-aminoimidazole and imidazoline derivatives through a three-step process.

1,2‐Di­methyl‐3‐(2‐nitro­phenyl)‐4,5‐di­hydro­imidazolium iodide

The crystal structure of 1,2Dimethyl-3(2nitro-phenyl)4,5dihydro-imidazolium iodide reveals a three-dimensional structure with intermolecular C-HO and C-HI hydrogen bonds.

REACTIONS OF 2,3-DIARYL-1-METHYL-4,5-DIHYDROIMIDAZOLIUM IODIDES WITH NUCLEOPHILIC REAGENTS

2,3-Diaryl imidazolium salts can be used to produce various products with one-carbon unit transfer, mimicking the one-carbon unit transfer function for tetrahydrofolate coenzymes.

AMINOLYSIS OF 1,2-DIMETHYL- 3-ARYLSULFONYL-4,5-DIHYDROIMIDAZOLIUM IODIDES WITH AROMATIC AMINES

This study demonstrates that arylsulfonylimidazolium salts can produce N′-aryl-N-methyl-N-(2-arylsulfonylamino)ethylacetamidine monohydroiodides in good to excellent yields through nu

NUCLEOPHILIC ADDITION TO 1,2-DIMETHYL-3-ARYLSULFONYL- 4,5-DIHYDROIMIDAZOLIUM IODIDES

This study demonstrates the high yield and excellent product formation of benzenesulfonamide derivatives from arylsulfonylimidazolium iodides with malononitrile or nitromethane anions.

A CONVENIENT SYNTHESIS OF IMIDAZOLIUM SALTS AND TRISUBSTITUTED ETHYLENEDIAMINE DERIVATIVES

This study demonstrates a convenient method for preparing imidazolium salts and trisubstituted ethylenediamine derivatives from commercially available 2-methyl-2-imidazoline, yielding high-yield products.

Ring-opening reactions of 2-imidazolines and their applications

2-imidazoline moiety's chemical instability enables diverse scaffold-generating and scaffold-morphing transformations under various conditions, expanding its applications in organic chemistry.

4.02 – Imidazoles

Imidazole chemistry has advanced significantly since 1995, with significant advances in reactivity, synthesis, and applications.

1,2‐Dimethyl‐3‐(2‐nitrophenyl)‐4,5‐dihydroimidazolium iodide