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.
| Publié dans: | Magnetic resonance in chemistry : MRC. - 1985. - 60(2022), 12 vom: 01. Dez., Seite 1157-1170 |
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| Auteur principal: | |
| Autres auteurs: | , , , , , |
| Format: | Article en ligne |
| Langue: | English |
| Publié: |
2022
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| 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... |
| Résumé: | © 2022 John Wiley & Sons Ltd. 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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| Description: | Date Completed 08.11.2022 Date Revised 04.01.2023 published: Print-Electronic Citation Status MEDLINE |
| ISSN: | 1097-458X |
| DOI: | 10.1002/mrc.5308 |