61764-86-1

Upstream product

• 67-56-1 methanol 
• 128993-40-8 2-benzoyl-1-benzyl-4,5-dihydroimidazole 
• 122-51-0 orthoformic acid triethyl ester 
• 4152-09-4 N-benzylethylenediamine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 109-94-4 formic acid ethyl ester 
• 288-32-4 1H-imidazole 
• 620-05-3 iodomethylbenzene 
• 128993-28-2 1-benzyl-2-(1-hydroxy-1-phenylethyl)-4,5-dihydroimidazole 
• 128993-32-8 1-benzyl-2-(1-hydroxy-1-phenylpropyl)-4,5-dihydroimidazole 
• 128993-29-3 1-benzyl-2-(1-hydroxy-1-phenylpentyl)-4,5-dihydroimidazole 
• 128993-30-6 1-benzyl-2-(diphenylhydroxymethyl)-4,5-dihydroimidazole 
• 128993-24-8 1-benzyl-2-(phenylhydroxymethyl)-4,5-dihydroimidazole 
• 128993-33-9 1-benzyl-2-(1-hydroxy-1-phenylnonyl)-4,5-dihydroimidazole 

Downstream Products

• 128993-30-6 1-benzyl-2-(diphenylhydroxymethyl)-4,5-dihydroimidazole 
• 128993-23-7 1-benzyl-2-(1-hydroxydecyl)-4,5-dihydroimidazole 
• 128993-41-9 1-benzyl-2-hexanoyl-4,5-dihydroimidazole 
• 128993-36-2 1-benzyl-2-(1-ethyl-1-hydroxyprop-2-enyl)-4,5-dihydroimidazole 
• 128993-42-0 1-benzyl-2-decanoyl-4,5-dihydroimidazole 
• 128993-40-8 2-benzoyl-1-benzyl-4,5-dihydroimidazole 
• 2385-38-8 1-benzyl-2,3,4,5-tetrahydroimidazol-2-one 
• 128993-58-8 1-benzyl-2-(4-methylphenylthio)-4,5-dihydroimidazole 
• 128993-37-3 1-benzyl-2-(1-hydroxycyclohex-1-yl)-4,5-dihydroimidazole 
• 128993-24-8 1-benzyl-2-(phenylhydroxymethyl)-4,5-dihydroimidazole 
• 128993-44-2 1-benzyl-2-[phenyl(tert-butyldimethylsilyloxy)methyl]-4,5-dihydroimidazole 
• 128993-26-0 1-benzyl-2-(4-methoxyphenylhydroxymethyl)-4,5-dihydroimidazole 
• 128993-27-1 1-benzyl-2-(3,4-dimethoxyphenylhydroxymethyl)-4,5-dihydroimidazole 
• 128993-43-1 1-benzyl-2-(1-tert-butyldimethylsilyloxybutyl)-4,5-dihydroimidazole 

Relevant academic research and scientific papers

Coenzyme-inspired chemistry 1: The C-2 alkylation of 4,5-dihydroimidazoles

Alkylation of 4,5-dihydroimidazoles at C-2 is accomplished using a double umpolung of the reactivity of that position, via sulfenylation of a nucleophilic C-2 lithio-species and substitution using an alkyl nucleophile. Arylation via unexpected sulfide con

Mercury (II), copper (II) and silver (I) complexes with ether or diether functionalized bis-NHC ligands: Synthesis and structural studies

The oligoether-linked dibenzimidazolium (or diimidazolium) salts, bis[2-(3-ethylbenzimidazolium-1-yl)ethyl]ether diiodide (1), bis[2-(3- nbutylbenzimidazolium-1-yl)ethyl]ether diiodide (2), 1,1′-[1,2-ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3-benzylbenzimidazolium- 1-yl) diiodide (3), 1,1′-[1,2-ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3- ethylbenzimidazolium-1-yl) di-hexafluorophosphate (4), 1,1′-[1,2- ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3-benzylimidazolium-1-yl) diiodide (5), and their five mercury(ii), copper(ii) and silver(i) complexes with ether or diether linkers mercury-{C,C′-bis[2-(3-ethylimidazolin-2-yliden-1-yl) ethyl]ether} tetraiodomercurate (7), copper-{C,C′-bis[2-(3- nbutylimidazolin-2-yliden-1-yl)ethyl]ether} tetraiodomercurate (8), mercury-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-benzylbenzimidazolin-2-yliden-1-yl)} triiodomercurate acetate (9), silver-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-ethylbenzimidazolin-2-yliden-1-yl)} hexafluorophosphate (10) and mercury-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-benzylimidazolin-2-yliden-1-yl)} tetraiodomercurate (11), as well as one anionic complex bis[2-(3-nbutylbenzimidazolium-1-yl)ethyl]ether di-μ-iodo-bis(diiodomercurate) (6) were prepared and characterized. Each of N-heterocyclic carbene metal complexes 7-11 possesses a macrometallocycle, respectively, formed by one metal atom and one bidentate chelate carbene ligand. In the crystal packing of complexes 6-11, 2D supramolecular layers are formed via intermolecular weak interactions, including π-π interactions, hydrogen bonds, C-H...π contacts and weak Hg...I bonds.

Robust and electron-rich cis-palladium(II) complexes with phosphine and carbene ligands as catalytic precursors in Suzuki coupling reactions

A new imidazolinium ligand precursor [L2H]Cl (2) was prepared in 86 % yield. Compared with its imidazolium counterpart, [L1H]Cl (1), 2 is very sensitive to moisture and can undergo ring-opening reactions very readily. Palladium complexes with the ring-opened products from imidazolinium salts were isolated and characterized by X-ray crystallography. Theoretical studies confirmed that the imidazolinium salt has a higher propensity for the ring-opening reaction than the imidazolium counterpart. New mixed phosphine/carbene palladium complexes, Cis-[PdCl2(L)(PR3)] (L = L1 and L2; R = Ph. Cy). were successfully prepared. These complexes are highly robust as revealed by variable-temperature NMR spectroscopic studies and thermal gravimetric analysis. The structural and electronic properties of the new complexes on varying the carbene group (imidazol-2-ylidene group (unsaturated carbene) vs. imidazolin-2-ylidene (saturated carbene)) and the phosphine group (PPh3 vs. PCy 3) were studied in detail by X-ray crystallography, X-ray photoelectron spectroscopy, and theoretical calculations. The catalytic study reveals that Cis-[PdCl2(L2)-(PCy3)] is a competent PdII precatalyst for Suzuki coupling reactions, in which unreactive aryl chlorides can be applied as substrates.

Oxidative decarboxylative synthesis of 2-H-imidazolines from glyoxylic acid and 1,2-diamines

A novel method to prepare 2-H-imidazolines from glyoxylic acid monohydrate and 1,2-diamines is described; the key reaction of this method is the oxidative decarboxylation of the 2-carboxy imidazolidines by NBS. The Royal Society of Chemistry.

Competitive amide hydrolysis in mono- and diformylated ethylenediamines

Alkaline hydrolysis of formylated ethylenediamines of the general structure R1-N(X)-CH2CH2-N(CHO)-R2 (R 1, R2 = H, benzyl, benzoyl; X = H, CHO) was studied in mild conditions. Breaking of the N-C amide bonds took place easily for HN-CHO or (benzoyl)N-CHO, hardly for (benzyl)N-CHO, and did not occur at all for N-COPh. Generally speaking, the various amide bonds underwent hydrolysis according to the following qualitative order of increasing reactivity: PhCO-N(H or alkyl)(alkyl or CHO) ?HCO-N(alkyl)2 1H- and 13C-NMR features of all compounds of interest are presented and discussed. Hindered rotation about the C-N amide bond(s) caused E/Z isomerism in mono- and diformylated derivatives.

Annulation of dihydroimidazoles: A 1,3-dipolar cycloaddition route to pyrrolo[1,2-a]imidazoles, pyrrolidines and pyrroles

4,5-Dihydroimidazolium ylides, formed by N-alkylation of 4,5-dihydroimidazoles, undergo diastereoselective endo 1,3-dipolar cycloaddition with electron-deficient alkene dipolarophiles to afford hexahydropyrrolo[1,2-a]imidazoles; reduction of the aminal fu

Synthesis and characterisation of 1-alkyl-2-imidazoline complexes of noble metals; crystal structure of trans-[PtCl2{N=C(H)N(Et)CH2CH2}(PEt 3)]

Treatment of a 1-alkyl-2-imidazoline N(R)(CH2)2N=CH with a μ-dichloro-dirhodium(I) or -diplatinum(II) complex [{Rh(μ-Cl)(cod)}2] or [{Pt(μ-Cl)Cl(PEt3)}2] gave the mononuclear 1-alkyl-2-imidazoline complex [RhCl{N=C(H)N(R)CH2CH2)(cod)] (R = Et 1a or CH2Ph 1b) or trans[PtCl2{N=C(H)N(R)CH2CH2}(PEt3)] (R = Et 2a or CH2Ph 2b) (cod = cycloocta-1,5-diene). A single-crystal X-ray diffraction study of 2a revealed it to have a square-planar geometry about platinum, the imidazoline ring being coplanar with this plane, and a Pt-N distance of 2.088(11) A; the Pt-P bond length of 2.231(4) A indicates that the imidazoline ligand has a marginally stronger trans influence than analogues of its isomer such as CN(R)(CH2)2NR. The rhodium complexes 1a and 1b have been shown to catalyse cyclopropanation of styrene and ethyl diazoacetate in high yields.

Thiamine coenzyme models: Imidazolinium ylides and the reactions of 2-(hydroxyalkyl)imidazolines

Ketones are prepared from aldehydes via 1-benzyl-2-(1-hydroxyalkyl)-2-imidazolines (adducts of the aldehydes with 1-benzyl-2-lithio-2-imidazoline) whereas 1-benzyl-2-(1-oxoalkyl)-2-imidazolines act as acyl transfer reagents; imidazolinium ylides are intermediates in both processes.

Tetrahydrofolate coenzyme models: Imidazolines as nucleophilic C1-transfer reagents

1-Benzyl-2-imidazoline is deprotonated at C-2 and alkylated by a sulphenylation-substitution sequence (to complete a formal C1-transfer), whereas arylation occurs by an unusual sulphenylation-sulphide contraction pathway.

Annulation of imidazolines: A 1,3-dipolar cycloaddition route to pyrroloimidazoles, pyrrolidines and pyrroles

Azomethine ylides, prepared from imidazolinium salts, undergo 1,3-dipolar cycloaddition with a variety of dipolarophiles to produce hexahydropyrrolo[1,2-α]imidazoles, which are reduced to pyrrolidines; with 2-chloroacrylonitrile as dipolarophile, pyrroles