Photoluminescence studies of molecular interactions. Part I. Synthesis of some indolyl ketones and tryptophan analogues

Abstract

A number of indolyl ketones and an amino-acid have been prepared by Fischer indolisation of cyclic diketones and of their monoethylene acetals: the difficultly accessible 1,2,4,9-tetrahydrocarbazol-3-one (1) and the novel amino-acid 3-amino-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid (5) were obtained in good yield in this way. The direction of indolisation of decalin-2,6-dione monoethylene acetal and of 5α- and 5β-androstane-3,17-diones was established by mass spectrometry and shown to give linearly fused tetrahydrocarbazole derivatives.