engleski

Photochemistry of adamantane-phthalimides: a new method for the preparation of polycyclic derivatives of azepinones

Adamantane derivatives and polycyclic compounds with the similar structure have been a topic of research of synthetic and theoretical chemist for several decades. Not only that these molecules are characterized by a rigid structure which influences their reactivity, but they are also highly lipophilic resulting in a better transport through the cell membranes. Therefore, they have often been incorporated in the molecular structure of the biologically active molecules in order to increase the activity. Photochemical reaction of H-abstraction by phthalimides is a well-known reaction that has been used on various substrates giving rise to more complex molecules.[1, 2] In this report we present the photochemical transformation of two adamantane derivatives activated by phthalimide moieties.Whereas the photolysis of 1 results in domino-hydrogen abstractions giving rise to only one azepinone product, the photochemical reaction of 2 gives two products resulting from the H-abstractions from the different positions on the adamantane skeleton. The structure determination of the photoproducts, as well as the mechanism of the photochemical reaction will be discussed.

Photochemistry; adamantane-phtalimides; azepinones

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