Laboratoire de Constitution et Réaction de la Matière, UFR Sciences des Structures de la Matière et Technologie, Université Félix Houphouët Boigny de Cocody, Abidjan, Côte d'Ivoire.
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, Montréal, Québec, Canada.
Magn Reson Chem. 2022 Dec;60(12):1157-1170. doi: 10.1002/mrc.5308. Epub 2022 Sep 12.
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 ( H and C NMR) and 2D NMR (NOESY) spectroscopic analyses and high-resolution mass spectrometry (HRMS). The analysis of H NMR data performed at room temperature in deuterated dimethylsulfoxide (DMSO-d ) 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.
十八个新的含有咪唑并[1,2-a]吡啶骨架的 N-酰腙（9a-r）通过七步反应序列合成，最后是 2-（3-硝基-H-咪唑并[1,2-a]吡啶-2-基硫基）乙酰腙与各种苯甲醛衍生物（8a-r）缩合而成。所有合成的化合物均通过 1D NMR（ H 和 C NMR）和 2D NMR（NOESY）光谱分析和高分辨率质谱（HRMS）进行了表征。在室温下在氘代二甲亚砜（DMSO-d ）中进行的 H NMR 数据分析表明，（E）-2-（3-硝基-H-咪唑并[1,2-a]吡啶-2-基硫基）-N'-亚苄基乙二酰腙（9a-r）以两种构象的混合物存在，即顺式-并面 E（sp E）和反式-并面 E（ap E）。除了由邻羟基苯甲醛衍生的腙外，对于所有合成的 N-酰腙，发现 sp E 构象是主要形式。
