185850-13-9

Upstream product

• 40916-61-8 (S)-2-(methylamino)propan-1-ol hydrochloride 
• 185849-99-4 4-(2-Chloro-ethyl)-1-(toluene-4-sulfonyl)-1H-imidazole 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 163854-63-5 4-iodo-1-[(4-methylphenyl)sulfonyl]-1H-imidazole 
• 98-59-9 p-toluenesulfonyl chloride 
• 6429-10-3 4-(2-chloroethyl)-1H-imidazole hydrochloride 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 37622-92-7 1-(p-toluenesulfonyl)-1H-imidazole-4⁽⁵⁾-carboxaldehyde 
• 75927-49-0 pinacol vinylboronate 
• 185849-85-8 (S)-2-(3-methyl-2-butenyl-1-amino)-2-methylethanol 
• 185849-83-6 2-(3-methyl-2-butenyl-1-amino)ethanol 
• 6940-80-3 (S)-N-benzylalaninol 

Downstream Products

• 3718-04-5 4⁽⁵⁾-vinyl imidazole 
• 3262-89-3 triphenylboroxine 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Stille cross-coupling for the functionalization of the imidazole backbone: Revisit, improvement, and applications of the method

Abstract We have revisited the Stille coupling reaction for the functionalization of the imidazole backbone. In this context CuI was exploited as a co-catalyst, which resulted in significantly improved yields of target coupling products. Furthe

Functionalization of the Imidazole Backbone by Means of a Tailored and Optimized Oxidative Heck Cross-Coupling

A general and selective Pd-catalyzed cross-coupling of aromatic boronic acids with vinyl-imidazoles is disclosed. Unlike most cross-coupling reactions, this method operates well in absence of bases avoiding the formation of by-products. The reactivity is highly enhanced by the presence of nitrogen-based ligands, in particular bathocuproine. The method involves MnO2 as oxidant for the oxidation Pd (0)→Pd (II), a much weaker oxidant than previously reported in the literature. This allows for the use of reactants that possess a multitude of functional groups. A scope and limitation study involving a series of 24 boronic acids, whereof 18 afforded TMs in yields in the range 41–95%. The disclosed method constitutes the first general method for the oxidative Heck cross-coupling on the imidazole scaffold, which moreover operates with a selection of other heterocycles. (Figure presented.).

Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors

A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads. The analysis of theoretical and experimental descriptors revealed correlations between the electronic properties of the heterocyclic cores and their reactivity against GSH that are helpful in identifying suitable fragments for cysteines with specific nucleophilicity. The most important advantage of these fragments is that they show only minimal structural differences from non-electrophilic counterparts. Therefore, they could be used effectively in the design of targeted covalent inhibitors with minimal influence on key non-covalent interactions.

Preparation and diels-alder chemistry of 4-vinylimidazoles

(Chemical Equation Presented) Various 4-vinylimidazole derivatives have been prepared from the corresponding 4-iodoimidazoles or from urocanic acid. Several methods for the elaboration of these vinylimidazoles and their Diels-Alder reactions are reported. All of the vinylimidazoles prepared in the course of this study react with N-phenylmaleimide quite readily with mild thermal activation providing a single cycloadduct, in most cases the initial, nonaromatic adduct. With more electron rich substrates, there is a tendency for these initial cycloadducts to undergo aromatization, ene reaction, and oxidation although this can be circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with dimethyl acetylene dicarboxylate. These substrates also participate in regioselective Diels-Alder reactions with monoactivated dienophiles, but require fairly forcing conditions, thus only providing the aromatized cycloadducts in modest yields. An investigation of substituent effects at the 2-position of the imidazole moiety was undertaken, in which electron-donating and weakly electron-withdrawing substituents are tolerated. In addition, several substrates with terminally substituted vinyl moieties have been investigated.

Synthesis and Diels-Alder reactions of 4-vinylimidazoles

(equation presented) The synthesis of several 4-vinylimidazoles via Stille cross-coupling reactions of the corresponding protected 4-iodoimidazoles with tributylvinylstannane is described. These heterocyclic dienes are shown to be effective partners in th

Imidazo[1,5-g][1,4]diazepines, TIBO analogues lacking the phenyl ring: Synthesis and evaluation as Anti-HIV agents

The imidazo[1,5-g][1,4]diazepine derivatives 7a and 7b, analogues of TIBO lacking the aromatic ring, were prepared as part of a research program to find compounds displaying antiviral activity against HIV-2 and resistant strains of HIV-1. Condensation of N-trityl and N-tosyl 4-(2-chloroethyl)imidazole with the appropriate amino alcohols gave compounds 10a-e and 16a-e. The hydroxyl group in these intermediates was activated toward closure of the [1,4]diazepine ring by either conversion to the corresponding chloro derivative, or by N → O transfer of the tosyl group. However, only cyclization to compounds 13a and 13b proved efficient. These products were converted to the target molecules 7 by reaction of their C-2 anion with Sg. In vitro evaluation of compounds 7a,b and 13a,b in cell culture (GEM SS/HIV-1-LAI and CEM SS/HIV 1 nevirapine resistant cells) revealed that only 13b displayed minimal activity.