One‐Pot Synthesis of Highly Fluorescent Pyrido[1, 2‐a]indole Derivatives through CH/NH Activation: Photophysical Investigations and Application in Cell Imaging. Issue 44 (11th September 2014)

• Record Type: Journal Article
• Authors: Samala, Srinivas; Pallavi, Pragyan; Kumar, Ravi; Arigela, Rajesh K; Singh, Gajendra; Ampapathi, Ravi Sankar; Priya, Amulya; Datta, Sunando; Patra, Abhijit; Kundu, Bijoy
• Is Part Of: Chemistry. Volume 20:Issue 44(2014)
• Page Start: 14344
• Page End: 14350
• Publication Date: 2014-09-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201404189
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We describe a straightforward strategy for the synthesis of strongly fluorescent pyridoindoles by Pd‐catalyzed oxidative annulations of internal alkynes with C‐3 functionalized indoles through CH/NH bond activation in a one‐pot tandem process. Mechanistic investigations reveal the preferential activation of NH indole followed by CH activation during the cyclization process. Photophysical properties of pyridoindoles exhibited the highest fluorescence quantum yield of nearly 80 %, with emission color varying from blue to green to orange depending on the substructures. Quantum mechanical calculations provide insights into the observed photophysical properties. The strong fluorescence of the pyrido[1, 2‐<italic>a</italic>]indole derivative has been employed in subcellular imaging, which demonstrates its localization in the cell nucleus.</p> </abstract>