A simple and convenient one-pot method for the preparation of heteroaryl-2-imidazoles from nitriles

Voss, Matthew E.; Beer, Catherine M.; Mitchell, Scott A.; Blomgren, Peter; Zhichkin, Paul E.

doi:10.1016/j.tet.2007.11.009

Cited by 51 publications

(34 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…2,6-Bis(1H-imidazol-2-yl)pyridine (H 2 dimpy) was synthesized following procedures described in the literature (Voss et al, 2008;Hashiguchi et al, 2010;Rigsby et al, 2012), with minor modifications (see the supporting information for a detailed description). Single crystals suitable for diffraction analysis were obtained by slow recrystallization from a methanol-water (3:1 v/v) solution for compound I and a methanol-HCl (0.1 mol l À1 ) (9:1 v/v) solution for compound II, by dissolving 10 mg of H 2 dimpy in 5 ml of the corresponding mixture and placing it in a 10 ml vial with a needleperforated lid at room temperature for 5 d, after which time the crystals were collected.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Analysis of solvent-accessible voids and proton-coupled electron transfer of 2,6-bis(1H-imidazol-2-yl)pyridine and its hydrochloride

et al. 2019

View full text Add to dashboard Cite

The crystal structures of the solid form of solvated 2,6‐bis(1H‐imidazol‐2‐yl)pyridine (H2dimpy) trihydrate, C11H9N5·3H2O·[+solvent], I, and its hydrate hydrochloride salt 2‐[6‐(1H‐imidazol‐2‐yl)pyridin‐2‐yl]‐1H‐imidazol‐3‐ium chloride trihydrate, C11H10N5+·Cl−·3H2O, II, are reported and analysed in detail, along with potentiometric and spectrophotometric titrations for evaluation of the acid–base equilibria and proton‐coupled electron‐transfer reactions. Compound I crystallizes in the high‐symmetry trigonal space group P3221 with an atypical formation of solvent‐accessible voids, as a consequence of the 32 screw axis in the crystallographic c‐axis direction, which are probably occupied by uncharacterized disordered solvent molecules. Additionally, the trihydrated chloride salt crystallizes in the conventional monoclinic space group P21/c without the formation of solvent‐accessible voids. The acid–base equilibria of H2dimpy were studied by potentiometric and spectrophotometric titrations, and the results suggest the formation of H3dimpy+ (pKa1 = 5.40) and H4dimpy2+ (pKa2 = 3.98), with the electrochemical behaviour of these species showing two consecutive irreversible proton‐coupled electron‐transfer reactions. Density functional theory (DFT) calculations corroborate the interpretation of the experimental results and support the assignment of the electrochemical behaviour.

show abstract

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Analysis of solvent-accessible voids and proton-coupled electron transfer of 2,6-bis(1H-imidazol-2-yl)pyridine and its hydrochloride

et al. 2019

View full text Add to dashboard Cite

show abstract

“…All chemicals were commercially available and used as received without further purification. The starting materials compound 3 to 12 were prepared by the literature method . Melting points were determined on a Mel‐Temp melting point apparatus and are uncorrected.…”

Section: Methodsmentioning

confidence: 99%

Syntheses of Symmetric and Unsymmetric Bis‐imidazole Derivatives Using Phase‐Transfer Catalysis

Kun-peng

Jin

Zhou

et al. 2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A convenient method for the preparation of symmetric and unsymmetric bisimidazole derivatives was established. The symmetric bisimidazolylmethane derivatives 1a–9a was prepared with 2‐substituted imidazole derivatives 1–9 as reaction materials. However, the symmetric and unsymmetric bisimidazolylmethane derivatives 10a–12a and 10b–12b was obtained, respectively. With 4‐position with the azo‐groups imidazole derivatives 10–12 were used as reaction materials. All these compounds have been structurally characterized by the NMR, ESI‐MS, and EA. And 8a and 12a were also characterized by the X‐ray single crystal diffusion.

show abstract

“…Imidazolen, [271] 1,2,4-Triazolen, [272] Tetrazolen [273] oder Thiazolen, [274] genutzt werden. [275] Die …”

Section: Synthese Via Kondensations-und Cycloadditionsreaktionenunclassified

Totalsynthese von Nosiheptid

Wojtas

Riedrich

et al. 2016

Angewandte Chemie

View full text Add to dashboard Cite

Eine Totalsynthese des bismakrocyclischen Thiopeptidantibiotikums Nosiheptid gelang durch den Aufbau einer voll funktionalisierten linearen Vorstufe und konsekutive Makrocyclisierungen. Schlüsselmerkmale waren eine kritische Makrothiolactonisierung und eine milde Entschützungsstrategie für den 3‐Hydroxypyridin‐Kern. Der Naturstoff war mit isoliertem authentischem Material im Hinblick auf spektroskopische Daten und antimikrobielle Aktivität identisch.

show abstract

A simple and convenient one-pot method for the preparation of heteroaryl-2-imidazoles from nitriles

Cited by 51 publications

References 34 publications

Analysis of solvent-accessible voids and proton-coupled electron transfer of 2,6-bis(1H-imidazol-2-yl)pyridine and its hydrochloride

Analysis of solvent-accessible voids and proton-coupled electron transfer of 2,6-bis(1H-imidazol-2-yl)pyridine and its hydrochloride

Syntheses of Symmetric and Unsymmetric Bis‐imidazole Derivatives Using Phase‐Transfer Catalysis

Totalsynthese von Nosiheptid

Contact Info

Product

Resources

About