engleski

Photodecarboxylation of different aminoadamantane carboxylic acids activated by phthalimides

Phthalimide is a versatile chromophore that undergoes different photochemical reactions which have been applied in organic synthesis [1]. The phototochemical reactions of phthalimide include electron transfer, inter- and intramolecular H-abstractions, photoreductions, and [2+2] cycloadditions [2]. We have recently investigated photodecarboxylation of 3-(N-phthalimido)adamantane-1-carboxylic acid (1)[3]. It was demonstrated that adamantyl radical formed in the decarboxylation can be trapped with electron defficient alkenes. In continuation of that research, we have synthesized novel phthalimide derivatives of aminoadamantane carboxylic acids 2 and 3, and investigated their photochemical reactivity in the decarboxylation reactions. The molecules were designed to probe for the influence of molecular structure to the photodecarboxylation efficiency. Whereas 2 undergoes only decarboxylation giving 4, 1, 2-disubstituted derivative 3 gives cyclized benzodiazepinone product 5 as the major product.

Photodecarboxylation; aminoadamantane carboxylic acid; phthalimide chromophore

nije evidentirano