33722-46-2

Usage

General Description

1H-Imidazole, 4,5-dihydro-2,4,5-triphenyl, (4R,5R)-rel- is a chemical compound with the molecular formula C21H19N. It is a stereochemically defined form of imidazole, a heterocyclic aromatic organic compound. The (4R,5R)-rel- configuration refers to the stereochemistry of the compound, with the R and S designations denoting the spatial arrangement of substituent groups around the chiral center. 1H-Imidazole, 4,5-dihydro-2,4,5-triphenyl, (4R,5R)-rel- has potential applications in medicinal chemistry, material science, and organic synthesis due to its unique structural and electronic properties. It may be used as a building block in the synthesis of various organic compounds and pharmaceuticals.

Upstream product

• 92-29-5 hydrobenzamide 
• 703-55-9 1-naphthylmagnesiumbromide 
• 573-33-1 DL-(4R,5S)-2,4,5-triphenyl-4,5-dihydro-1H-imidazole 
• 54874-97-4 N-(erythro-α'-amino-bibenzyl-α-yl)-benzamide 
• 1140-29-0 N-(2-aminoethyl)-N-phenylaniline 
• 100-52-7 benzaldehyde 
• 57-13-6 urea 
• 65-85-0 benzoic acid 
• 951-87-1 meso-1,2-diphenyl-1,2-diaminoethane 
• 92-29-5 (E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene 
• 573-33-1 (4R,5S)-2,4,5-Triphenyl-4,5-dihydro-1H-imidazole 
• 16118-22-2 benzylidenamine 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 80424-18-6 (4R,5R)-2,4,5-Triphenyl-imidazolidine 

Downstream Products

• 1140-29-0 N-(2-aminoethyl)-N-phenylaniline 
• 91840-93-6 (1S,2S)-N,N'-diethyl-1,2-diphenyl-1,2-ethanediamine 
• 216861-21-1 (1S,2S)-N,N'-(1,2-diphenylethane-1,2-diyl)diacetamide 
• 58821-34-4 2r,3t,5,6-tetraphenyl-(6ξH)-7-oxa-1,4-diaza-bicyclo[4.1.0]hept-4-ene 
• 33722-47-3 DL-(4R,5S)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole 
• 911306-54-2 (+)-(1S,2S)-N-[(R)-α-acetoxyphenylacetyl]-N'-benzoyl-1,2-diamino-1,2-diphenylethane 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 161970-92-9 (+)-(4R,5R)-2,4,5-triphenyl-trans-4,5-dihydroimidazole 
• 133815-20-0 (-)-(4S,5S)-4,5-dihydro-2,4,5-triphenyl-1H-imidazole 
• 911306-52-0 (-)-(4S,5S)-1-[(R)-α-acetoxyphenylacetyl]-4,5-dihydro-2,4,5-triphenyl-1H-imidazole 
• 40102-64-5 racem.-1,2-diphenyl-ethane-1,2-diamine; dihydrochloride 
• 102457-31-8 (+/-)-2,4r,5t-tricyclohexyl-4,5-dihydro-1H-imidazole 
• 80424-18-6 (4R,5R)-2,4,5-Triphenyl-imidazolidine 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 

Relevant academic research and scientific papers

Convenient one-step synthesis of cis-2,4,5-triarylimidazolines from aromatic aldehydes with urea

A simple and efficient method has been developed for the synthesis of cis-2,4,5-triarylimidazolines based on a one-step procedure of aldehydes and urea in the presence of cesium carbonate. Taylor & Francis Group, LLC.

Nuclear factor-κB mediated inhibition of cytokine production by imidazoline scaffolds

The mammalian nuclear transcription factor NF-κB is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-α) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-κB has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-κB mediated gene transcription in cell culture as well as inhibitors of TNF-α and IL-6 production in interleukin 1 beta (IL-1β) stimulated human blood.

Cycloaddition reactions of 1,3-diazabuta-1,3-dienes with alkynyl ketenes

The cycloaddition reactions of 'all-carbon' 1,3-diazabuta-1,3-dienes with a few conjugated and unconjugated alkynyl ketenes are described. The reactions provide some interesting azetidinones and dihydropyrimidinones bearing an alkynyl moiety. The regiochemistry of cycloadduct is related with the degree of conjugation of the alkynyl ketene. Moreover, two alternative approaches to 'all-carbon' 1,3-diazabuta-1,3-dienes are reported.

On the racemization of chiral imidazolines

(Chemical Equation Presented) Racemization of chiral imidazolines with base has been studied for the first time following an unexpected finding in the synthesis of chiral imidazoline ligands. Amine bases do not cause racemization. Strong inorganic bases can induce racemization, yet this occurs only when the nitrogen is unsubstituted, in agreement with a symmetry-allowed thermal disrotatory ring opening and closure from a diazapentadienyl anion. Surprisingly, even with electron-withdrawing N-substituents, no racemization is observed. Conditions which allow for the racemization-free manipulations of this important compound class have been defined and developed.

One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates

Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphatic aldehydes and N-nonsubstituted and N-monosubstituted 1,2-diamines. Furthermore, it was found that CH2Cl2 could be altered to TBME, a more environmentally friendly solvent, in the reaction using N-nonsubstituted 1,2-diamines. The reaction conditions were very mild and chemoselective.

A convenient preparation of enantiomerically pure (+)-(1R,2R)- and (-)-(1S,2S)-1,2-diamino-1,2-diphenylethanes

A gram-scale preparation of (1S,2S)- and (1R,2R)-1,2-diamino-1,2- diphenylethanes, (1S,2S)-1 and (1R,2R)-1, is reported via (±)-iso-amarine 4. Strategically, the activation of (±)-iso-amarine 4 for hydrolysis to the required diamines and enantiomeric resolution is achieved simultaneously by formation of two separable diastereoisomeric N-acylamidines 5 and 6 derived from direct DCC-mediated coupling of (±)-iso-amarine 4 with (R)-acetylmandelic acid. iso-Amarine 4 is conveniently obtained from amarine 3, and a one-pot synthesis of the latter is reported from benzaldehyde and hexamethyldisilazane as catalysed by benzoic acid.

Alumina-ammonium acetate as an efficient reagent for the one-pot synthesis of cis-2,4,5-triarylimidazolines from aromatic aldehydes

A simple, efficient, and new method has been developed for the synthesis of 2,4,5-triarylimidazolines from aldehydes through a one-pot reaction of aldehydes in the presence of alumina-ammonium acetate under solvent-free conditions using microwave irradiation. This method is easy, rapid, one-pot and good to high-yielding reaction for the synthesis of 2,4,5-triarylimidazolines.

Synthesis and SAR of novel 4,5-diarylimidazolines as potent P2X7 receptor antagonists

The synthesis and SAR of a series of potent P2X7 receptor antagonists is described. The synthesis featured high-throughput solution- and solid-phase techniques including a microwave induced imidazoline formation. A series of 4,5-diarylimidazoline libraries were prepared using high-throughput solid-phase and microwave techniques. The compounds were evaluated as P2X 7 antagonists and their SAR is described.

Synthesis of N,N-di(arylmethylidene)arylmethanediamines by flash vacuum pyrolysis of arylmethylazides

Flash vacuum pyrolysis of arylmethylazides 7a-d gave 2,4-diazapentadienes 5a-d in high yield (76-92%). The thermal cyclization of 5a-d gave cis-imidazolines 1a-d, further heating or Swern oxidation of 1a-d gave dehydrogenated products, imidazoles 2a-d.

Studies on the synthesis of 1-aminoalkylphosphonates from aldehydes using silica-supported ammonium hydrogen carbonate

Studies on the use of silica-supported ammonium hydrogen carbonate as an efficient reagent for the synthesis of 1-amino-phosphonates under microwave irradiation in solvent-free conditions is reported. Investigations showed that this reaction proceeds by the formation of methanediamine as an intermediate. The reaction in the absence of diethyl phosphite gave cis-imidazolines as the major products.