Synthesis and characterization of novel conformers of (E)-2-(3-nitro-H-imidazo[1,2-a]pyridin-2-ylthio)-N'-benzylideneacetohydrazide derivatives

© 2022 John Wiley & Sons Ltd.

Détails bibliographiques
Publié dans:Magnetic resonance in chemistry : MRC. - 1985. - 60(2022), 12 vom: 01. Dez., Seite 1157-1170
Auteur principal: Ablo, Evrard (Auteur)
Autres auteurs: Coulibaly, Souleymane, Coulibali, Siomenan, Signo, Kouassi, Achi, Patrick-Armand, Giraud, Nicolas, Bertho, Gildas
Format: Article en ligne
Langue:English
Publié: 2022
Accès à la collection:Magnetic resonance in chemistry : MRC
Sujets:Journal Article 13C 1H 2D-NOESY NMR in DMSO-d6 N-acyl-hydrazones benzaldehydes conformational analysis hydrazide-hydrazones imidazo[1,2-a]pyridine Hydrazones plus... Dimethyl Sulfoxide YOW8V9698H
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245 1 0 |a Synthesis and characterization of novel conformers of (E)-2-(3-nitro-H-imidazo[1,2-a]pyridin-2-ylthio)-N'-benzylideneacetohydrazide derivatives 
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520 |a Eighteen new N-acylhydrazones (9a-r) containing the imidazo[1,2-a]pyridine scaffold were synthesized through a seven steps reaction sequence, ending with a condensation of 2-(3-nitro-H-imidazo[1,2-a]pyridin-2-ylthio)acetohydrazide with various benzaldehyde derivatives (8a-r). All synthesized compounds were characterized by 1D NMR (1 H and 13 C NMR) and 2D NMR (NOESY) spectroscopic analyses and high-resolution mass spectrometry (HRMS). The analysis of 1 H NMR data performed at room temperature in deuterated dimethylsulfoxide (DMSO-d6 ) revealed the presence of (E)-2-(3-nitro-H-imidazo[1,2-a]pyridin-2-ylthio)-N'-benzylideneacetohydrazide (9a-r) as a mixture of two conformers, namely, syn-periplanar E (sp E) and anti-periplanar E (ap E). For all N-acylhydrazones that were synthesized, the sp E conformer was found to be the major form except in the case of hydrazone derived from o-hydroxybenzaldehyde 
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650 4 |a conformational analysis 
650 4 |a hydrazide-hydrazones 
650 4 |a imidazo[1,2-a]pyridine 
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700 1 |a Coulibaly, Souleymane  |e verfasserin  |4 aut 
700 1 |a Coulibali, Siomenan  |e verfasserin  |4 aut 
700 1 |a Signo, Kouassi  |e verfasserin  |4 aut 
700 1 |a Achi, Patrick-Armand  |e verfasserin  |4 aut 
700 1 |a Giraud, Nicolas  |e verfasserin  |4 aut 
700 1 |a Bertho, Gildas  |e verfasserin  |4 aut 
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