| Synthesis of Adamatane Modified Polyhydroquinolines |
| کد مقاله : 1156-ICOC |
| نویسندگان |
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علی رستمی نیری *1، عادله مشتقی زنوز2 1شیمی آلی دانشکده علوم پایه دانشگاه شهید مدنی آذربایجان 2دانشگاه شهید مدنی آذربایجان |
| چکیده مقاله |
| Diamondoids constitute a unique class of cage-like saturated hydrocarbons characterized by exceptional rigidity, high thermal stability, and well-defined three-dimensional architectures, making them attractive building blocks in advanced molecular design [1]. Among these structures, adamantane—the simplest and most extensively investigated diamondoid—has gained substantial attention due to its pronounced lipophilicity, steric bulk, and its documented ability to modulate both the physicochemical and biological properties of hybrid organic molecules [2]. The incorporation of rigid, lipophilic adamantane units into heterocyclic frameworks has emerged as a powerful strategy for improving the physicochemical and pharmacokinetic profiles of bioactive molecules. In this study, the reaction of dimedone with a series of adamantane-containing benzylidene derivatives was systematically investigated to construct new adamantane-dihydropyridine structures. The synthetic route began with the preparation of N-1-adamantyl acetoacetamide, which underwent condensation with various substituted benzaldehydes to afford a set of benzylidene intermediates. Subsequent Hantzsch-type multicomponent cyclocondensation of these intermediates with dimedone and ammonium acetate provided a library of 4,1-dihydropyridine derivatives bearing the adamantane scaffold (Scheme 1). The structures of all products were confirmed by FT-IR, ¹H NMR, and ¹³C NMR spectroscopy. |
| کلیدواژه ها |
| Quinoline, Adamantane, Diamondoid, Hybrid Compounds |
| وضعیت: پذیرفته شده |