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Abstract
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Diamondoids are cage-saturated hydrocarbon molecules and superimposable on the diamond lattice, which can be described as hydrogen-terminated nanodiamonds [1]. Adamantane with the C10H15 formula is the smallest diamondoid. In addition to the existence of eight adamantane-based drugs in the world pharmaceutical market, the unique properties of adamantane, including the size, lipophilicity, rigidity, and biocompatibility make it special for modification of known drugs through an add-on strategy [2]. Hence, we decided to synthesize novel tetrahydrobenzo[b]pyrans and polyhydroquinolines derivatives incorporating an adamantane moiety. For this purpose, firstly N-1-adamantyl-2-(arylidene) acetoacetamides I were synthesized from the Knoevenagel reaction of N-1-adamantyl acetoacetamide 1 and aromatic aldehydes [3]. Then sequential Michael addition/cyclizatin reaction of arylidene derivatives I with dimedone or enaminone 2 afforded 4H-chromene derivatives II and polyhydroquinolines derivatives III, respectively
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