The Synthesis Of Novel Indole Derivatives And Its Applications

The charpter one focused on the discussion of transition metal -catalyzed or organocalyst -promote functionalization of indole. Transition metal -catalyzed carbon-carbon bond or carbon-heteroatom bond-forming transformation is one of the most important pathways in organic synthesis. The transition metal -catalyzed reactions with high efficiency, simple and good regioselectivity, have been widely used to construct new C-C bond or C-heteroatombond. In this charpter, the current issues of the transition metal -catalyzed C-H activation of indole and its derivatives is provided. And then we descriped the transition metal -catalyzed N-H functionalization reaction on indole skeleton. Finally, we made a brief overview for the synthesis of the chiral indole derivatives by organic asymmetric catalysis, which based on shortcomings of transition metal catalysis and the concept of green chemistry in organic synthesis reactions.The one-pot iron-catalyzed cycloaddition of indole and o-phthalaldehyde afforded indolyl benzo[b]carbazoles via sequential carbon-carbon bond-forming addition, cyclization involving intramolecular alkylation and aromatization forming a benzene ring. In addition, the fluorescence properties of such indolyl benzo[b]carbazoles were also investigated, in which it showed significant changes in fluorescent intensity upon addition of trimethylchlorosilane (TMSC1) or trifluoroacetic acid (TFA).A simple and efficient methylthiolation protocol was successfully established for the synthesis of ketone-substituted indoles bearing 3-methylthioether moiety. The new synthetic approach featured with metal-free oxidation and methylthiolation of alcohol-containing indoles, in which new C-S bond and C=O bond were formed simultaneously using dimethyl sulfoxide as the sulfur source under the Swern oxidation conditions. The methylthiolation reaction provides a simple and facile procedure to methylthiolated indoles from readily available starting materials in good yields.