Base‐Mediated Reductive Coupling of Indole‐3‐tosylhydrazone with Thiols/Boronic Acids: Facile Synthesis of 3‐(phenylthio)methyl/benzyl Indole Derivatives. Issue 2 (13th January 2020)

• Record Type: Journal Article
• Authors: Khan, Imran; Sharma, Aanchal; Kamboj, Priya; Maity, Banibrata; Tyagi, Vikas
• Is Part Of: ChemistrySelect. Volume 5:Issue 2(2020)
• Page Start: 591
• Page End: 600
• Publication Date: 2020-01-13
• Subjects: Boronic acids -- benzylation -- catalyst-free -- indole -- methylthiolation -- photophysical properties -- thiols.; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201903863
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: 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 CH3 CN compared to water. Abstract : A base‐mediated reductive coupling of indole‐3‐tosylhydrazone with thiols/boronic acids to provide the biologically important 3‐(phenylthio)methyl/benzyl indole derivatives has been developed. This methodology has a number of advantages such as no use of transition metals, broad substrates scope and operational simplicity. Further, the photophysical properties of synthesized compounds were studied in different solvents.