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Synthesis of 1,3‐Disubstituted Imidazo[1,5‐ a ]pyridines through Oxidative C‐N Bond Formation from Aryl‐2‐pyridylmethanols and Their Fluorescent Study
Author(s) -
Chandrasekar Selvaraj,
Sangeetha Subramani,
Sekar Govindasamy
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901440
Subject(s) - chemistry , hypsochromic shift , bathochromic shift , intramolecular force , aryl , amination , oxidative phosphorylation , fluorescence , medicinal chemistry , alcohol , photochemistry , organic chemistry , combinatorial chemistry , catalysis , alkyl , biochemistry , physics , quantum mechanics
Abstract A simple, effortless, and efficacious protocol for the synthesis of highly fluorescing imidazo[1,5‐ a ]pyridines via copper catalyzed inter‐/intramolecular C−N bond formation between readily available pyridyl alcohols with either benzyl amines or amino acids has been developed. This domino reaction is involved with alcohol oxidation/condensation/oxidative amination sequence to synthesize imidazo[1,5‐ a ]pyridines in good to excellent yields. The fluorescence studies of these compounds indicated a bathochromic shift for the electron donating substituents, whereas a hypsochromic shift for the electron withdrawing substituents. Synthetic modification of the groups attached to the heterocyclic core showed a profound impact on the emission properties when subjected to pH and solvent polarity change.