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Base‐Mediated Reductive Coupling of Indole‐3‐tosylhydrazone with Thiols/Boronic Acids: Facile Synthesis of 3‐(phenylthio)methyl/benzyl Indole Derivatives
Author(s) -
Khan Imran,
Sharma Aanchal,
Kamboj Priya,
Maity Banibrata,
Tyagi Vikas
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903863
Subject(s) - indole test , bathochromic shift , chemistry , solvatochromism , enyne , photochemistry , fluorescence , combinatorial chemistry , quantum yield , trifluoromethanesulfonate , suzuki reaction , pyridine , solvent , organic chemistry , catalysis , palladium , physics , quantum mechanics
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 CH 3 CN compared to water.