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A transition-metal free base-mediated reductive coupling of indole-3-tosylhydrazone with thiols/boronic acids to afford biologically important 3-(phenylthio)methyl/benzyl indole derivatives has been developed. A number of advantages such as low cost, broad substrates scope and operational simplicity make it a potential method for the synthesis of 3- phenylthiomethyl/benzyl indole derivatives. Further, six derivatives were selected based on their electronic effects to study the photophysical properties in different solvents. The studied compounds exhibited strong solvatochromic shift and faces solvent dependent polarity in UV-Visible absorption as well as in fluorescence emission techniques. In addition, one derivative having -CN functionality exhibited most astonishing observation in fluorescence such as significant bathochromic shifting in the emission peak position as well as enhancing the fluorescence quantum yield in CH3CN compared to water.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles