Study of synthesis of 2‐(2‐alkoxyphenyl)‐1<i>H</i>‐imidazoles. Comparison of oxidative aromatization reactions of imidazolines

Pařík, Patrik; Šenauerová, Sylva; Lišková, Vlasta; Handlíř, Karel; Ludwig, Miroslav

doi:10.1002/jhet.5570430404

Cited by 16 publications

(2 citation statements)

References 27 publications

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“…As shown in Scheme , carboxyphthalimide 31 was amidated to form 4-cyanoanilide 32 , deprotected with hydrazine to form 33 , and then transformed into amino imidazoline 9 as described above. Diimidazole 12 was obtained by high-temperature Pd-catalyzed dehydrogenation of 2 .…”

Section: Results and Discussionmentioning

confidence: 99%

Antiprotozoal Selectivity of Diimidazoline N-Phenylbenzamides

et al. 2015

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We discovered three diimidazolines with high antiplasmodial selectivity that had IC50 values of 1.9-28 nM against cultured Plasmodium falciparum. We also identified a gem-dimethyl diimidazoline with high antitrypanosomal selectivity that had an IC50 value of 26 nM against cultured Trypanosoma brucei rhodesiense. Two 2-imidazoline heterocycles in a para orientation on a N-phenylbenzamide or similar core structure were required for high antiprotozoal activity. Ring expansion of the imidazoline as well as heterocyclic variants with pKa values of <7 all decreased activity significantly.

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Section: Results and Discussionmentioning

confidence: 99%

Antiprotozoal Selectivity of Diimidazoline N-Phenylbenzamides

et al. 2015

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“…Firstly, it is used for the oxidation of the starting alcohol 1 and secondly it is used in order to promote the aromatisation [20] of tetrahydrocarboline 5 , allowing effectively at least three operational steps to be carried out as part of a single cascade process.…”

Section: Introductionmentioning

confidence: 99%

Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine

Baiget¹,

Llona‐Minguez²,

Lang³

et al. 2011

Beilstein J. Org. Chem.

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SummaryThe carboline ring system is an important pharmacophore found in a number of biologically important targets. Development of synthetic routes for the preparation of these compounds is important in order to prepare a range of analogues containing the carboline heterocyclic moiety. A manganese dioxide mediated one-pot method starting with an activated alcohol and consisting of alcohol oxidation, Pictet–Spengler cyclisation, and oxidative aromatisation, offers a convenient process that allows access to β-carbolines. This one-pot process for the preparation of methyl 9H-pyrido[3,4-b]indole-1-carboxylate has subsequently been used as the key step in the synthesis of alangiobussinine and a closely related analogue.

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T‐Shaped Ionic Liquid Crystals Based on the Imidazolium Motif: Exploring Substitution of the C‐2 Imidazolium Carbon Atom

Goossens

Wellens

Hecke

et al. 2011

Chemistry A European J

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In this contribution the first examples of so-called rigid-core, T-shaped imidazolium ionic liquid crystals, in which the C-2 atom of the imidazolium ring is substituted with an aryl moiety decorated with one or two alkoxy chains, are described. The length of the alkoxy chain(s) was varied from six to eighteen carbon atoms (n=6, 10, 14-18). Whereas the compounds with one long alkoxy chain display only smectic A phases, the salts containing two alkoxy chains exhibit smectic A, multicontinuous cubic, as well as hexagonal columnar phases, as evidenced by polarising optical microscopy, differential scanning calorimetry, and powder X-ray diffraction. Structural models are proposed for the self-assembly of the molecules within the mesophases. The imidazolium head groups and the iodide counterions were found to adopt a peculiar orientation in the central part of the columns of the hexagonal columnar phases. The enantiotropic cubic phase shown by the 1,3-dimethyl-2-[3,4-bis(pentadecyloxy)phenyl]imidazolium iodide salt has a multicontinuous Pm ̄3m structure. To the best of our knowledge, this is the first example of a thermotropic cubic mesophase of this symmetry.

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Study of synthesis of 2‐(2‐alkoxyphenyl)‐1H‐imidazoles. Comparison of oxidative aromatization reactions of imidazolines

Cited by 16 publications

References 27 publications

Antiprotozoal Selectivity of Diimidazoline N-Phenylbenzamides

Antiprotozoal Selectivity of Diimidazoline N-Phenylbenzamides

Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine

T‐Shaped Ionic Liquid Crystals Based on the Imidazolium Motif: Exploring Substitution of the C‐2 Imidazolium Carbon Atom

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