16227-13-7

Upstream product

• 288-88-0 1,2,4-Triazole 
• 100-44-7 benzyl chloride 
• 41253-21-8 sodium triazole 
• 288-88-0 1,2,4-Triazole 
• 100-39-0 benzyl bromide 
• 122-51-0 orthoformic acid triethyl ester 
• 624-84-0 formic acid hydrazide 
• 100-46-9 benzylamine 
• 16227-06-8 {N'-[(dimethylamino)methylene]-N,N-dimethylhydrazonoformamide dihydrochloride} 
• 16227-06-8 (1E,N’E)-N’-((dimethylamino)methylene)-N,N-dimethylformohydrazonamide dihydrochloride 
• 622-78-6 Benzyl isothiocyanate 
• 177028-51-2 4-Benzyl-3-diethoxymethyl-4H-[1,2,4]triazole 

Downstream Products

• 1177251-07-8 1-{(4-benzyl-4H-1,2,4-triazol-3-yl)[4-(2-methyl-1,3-thiazol-4-yl)phenyl]methyl}-4-cyclobutyl-1,4-diazepane 
• 128136-96-9 1,4-dibenzyl-4H-1,2,4-triazol-1-ium bromide 

Relevant academic research and scientific papers

Cooperative 1D Triazole-Based Spin Crossover FeII Material with Exceptional Mechanical Resilience

A study reported the synthesis, the structural and magnetic characterizations, as well as the first accurate single crystal investigations of both high spin state (HS) and low spin state (LS) states of a new triazolebased spin crossover (SCO) Fe 1-D polymer [Fe(bntrz)3][Pt(CN)4]·H2O. The bntrz ligand was prepared in two steps by reaction of triethyl orthoformate with formylhydrazine and benzylamine under nitrogen atmosphere. Single crystals of [Fe(bntrz)3][Pt(CN)4]·H2O was synthesized via diffusion technique in a fine glass tube by layering an ethanolic solution of the bntrz ligand onto an aqueous solution containing both K2[Pt(CN) 4)]xH2O and Fe(BF4)2·6H2O salts.

Atom Transfer Radical Polymerization-Inspired Room Temperature (sp3)C-N Coupling

A simple nonphotochemical procedure is reported for Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and amides. The process is loosely based on the Goldberg reaction but takes place readily at room temperature. It uses Cu(I)Br, a commonly used and inexpensive atom transfer radical polymerization precatalyst, along with the cheap ligand N,N,N′,N″,N″-pentamethyldiethylenetriamine, to activate the R-X bond of the substrate via inner-sphere electron transfer. The procedure brings about productive C-N bond formation between a range of alkyl halide substrates with heterocyclic aromatic amines and amides. The mechanism of the coupling step, which was elucidated through application of computational methods, proceeds via a unique Cu(I) → Cu(II) → Cu(III) → Cu(I) catalytic cycle, involving (a) inner-sphere electron transfer from Cu(I) to the alkyl halide to generate the alkyl radical; (b) successive coordination of the N-nucleophile and the radical to Cu(II); and finally reductive elimination. In the absence of a nucleophile, debrominative homocoupling of the alkyl halide occurs. Control experiments rule out SN-type mechanisms for C-N bond formation.

Synthesis method of 1,2,4-triazole-3-carboxylic methyl ether

The invention provides a synthesis method of 1,2,4-triazole-3-carboxylic methyl ether and particularly relates to the technical field of pharmaceuticals. The synthesis method comprises the steps thatS1, 1,2,4-triazole, potassium carbonate or sodium carbon

Synthesis and Anti-proliferative Activity of N,N′-bis-substituted 1,2,4-Triazolium Salts against Breast Cancer and Prostate Cancer Cell Lines

A series of 1,4-N,N′-bis-substituted 1,2,4-triazolium bromide salts were synthesized and tested for anti-proliferative activity. 1,4-Bis(naphthalen-2-ylmethyl)-1,2,4-triazolium bromide (2) showed activity against MDA-MB-468 breast cancer and PC-3 prostate

Effect of N 4-substituent choice on spin crossover in dinuclear iron(II) complexes of bis-terdentate 1,2,4-triazole-based ligands

Seven new dinuclear iron(II) complexes of the general formula [Fe II2(PMRT)2](BF4)4· solvent, where PMRT is a 4-substituted-3,5-bis{[(2-pyridylmethyl)-amino]methyl}- 4H-1,2,4-triazole, have been prepared in order to investigate the substituent effect on the spin crossover event. Variable temperature magnetic susceptibility and 57Fe Moessbauer spectroscopy studies show that two of the complexes, [FeII2(PMPT)2](BF4) 4·H2O (N4 substituent is pyrrolyl) and [FeII2(PMPhAT)2](BF 4)4 (N4 is N,N-diphenylamine), are stabilized in the [HS-HS] state between 300 and 2 K with weak antiferromagnetic interactions between the iron(II) centers. Five of the complexes showed gradual half spin crossover, from [HS-HS] to [HS-LS], with the following T1/2 (K) values: 234 for [FeII2(PMibT)2](BF 4)4·3H2O (N4 is isobutyl), 147 for [FeII2(PMBzT)2](BF4) 4 (N4 is benzyl), 133 for [FeII 2(PMCF3PhT)2](BF4) 4·DMF·H2O (N4 is 3,5-bis(trifluoromethyl)phenyl), 187 for [FeII2(PMPhT) 2](BF4)4 (N4 is phenyl), and 224 for [FeII2(PMC16T)2](BF 4)4 (N4 is hexadecyl). Structure determinations carried out for three complexes, [FeII2(PMPT) 2](BF4)4·4DMF, [FeII 2(PMBzT)2](BF4)4·CH 3CN, and [FeII2(PMPhAT) 2](BF4)4·solvent, revealed that in all three complexes both iron(II) centers are stabilized in the high spin state at 90 K. A general and reliable 4-step route to PMRT ligands is also detailed.

Liquid ammonia as a dipolar aprotic solvent for aliphatic nucleophilic substitution reactions

The rate constants for the reactions of a variety of nucleophiles reacting with substituted benzyl chlorides in liquid ammonia (LNH3) have been determined. To fully interpret the associated linear free-energy relationships, the ionization constants of phenols ions in liquid ammonia were obtained using UV spectra. These equilibrium constants are the product of those for ion-pair formation and dissociation to the free ions, which can be separated by evaluating the effect of added ammonium ions. There is a linear relationship between the pKa of phenols in liquid ammonia and those in water of slope 1.68. Aminium ions exist in their unprotonated free base form in liquid ammonia and their ionization constants could not be determined by NMR. The rates of solvolysis of substituted benzyl chlorides in liquid ammonia at 25 °C show a Hammett ρ of zero, having little or no dependence upon ring substituents, which is in stark contrast with the hydrolysis rates of substituted benzyl halides in water, which vary 107 fold. The rate of substitution of benzyl chloride by substituted phenoxide ions is first order in the concentration of the nucleophile indicative of a SN2 process, and the dependence of the rate constants on the pKa of the phenol in liquid ammonia generates a Bronsted βnuc = 0.40. Contrary to the solvolysis reaction, the reaction of phenoxide ion with 4-substituted benzyl chlorides gives a Hammett ρ = 1.1, excluding the 4-methoxy derivative, which shows the normal positive deviation. The second order rate constants for the substitution of benzyl chlorides by neutral and anionic amines show a single Bronsted βnuc = 0.21 (based on the aqueous pKa of amine), but their dependence on the substituent in substituted benzyl chlorides varies with a Hammett ρ of 0 for neutral amines, similar to that seen for solvolysis, whereas that for amine anions is 0.93, similar to that seen for phenoxide ion.(Figure Presented)

DIAZEPANES AS HISTAMINE H3 RECEPTOR ANTAGONISTS

The invention relates to compounds of formula (I) wherein R1 to R8 and X1, X2 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.

An investigation into the alkylation of 1,2,4-triazole

The alkylation of 1,2,4-triazole with 4-nitrobenzyl halides and a variety of bases afforded the 1- and 4-alkylated isomers with a consistent regioselectivity of 90:10. Previously reported regiospecific alkylations of 1,2,4-triazole were re-examined and the quoted isomer ratios were shown to depend on the isolation procedure. The use of DBU as base in the alkylation of 1,2,4-triazole allows for a convenient and high yielding synthesis of 1- substituted-1,2,4-triazoles. (C) 2000 Elsevier Science Ltd.

Michael adducts in regioselective synthesis of N-substituted azoles

Michael adducts of azoles (4-phenyl-, 4-methyl- and 4-nitroimidazole, 4-methylbenzimidazole, 1,2,4-triazole and theophylline) are shown to be valuable substrates for obtaining the N-substituted derivatives of the parent heterocycles by a quaternization-Hofmann elimination sequence. The effectiveness of the procedure is dependent on the regiochemical outcome of the first, N-protective step, i.e. the Michael addition. By choosing the appropriate Michael acceptor, alkylating agent and deprotection conditions, the thermodynamically less stable regioisomers of N-substituted azoles have been obtained in high yields.