Open Access2‐(Alkylamino)‐3‐aryl‐6,7‐dihydrobenzofuran‐4( 5H )‐ones: Improved Synthesis and their Photophysical Properties
Author(s) -
Kumar Manoj,
Kumawat Lokesh Kumar,
Gupta Vinod Kumar,
Sharma Anuj
Publication year - 2015
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201500067
Subject(s) - aryl , dimedone , chemistry , aldehyde , isocyanide , luminescence , naked eye , absorption (acoustics) , solvent , photochemistry , organic chemistry , combinatorial chemistry , catalysis , alkyl , materials science , chromatography , detection limit , optoelectronics , composite material
Furans are an important class of compounds and exhibit a diverse range of activities and properties. As such, improved synthetic access to furans is an important research goal. In the present report, a solvent‐ and catalyst‐free reaction between 5,5‐dimethyl‐1,3‐cyclohexanedione (dimedone), an aryl aldehyde and an isocyanide under microwave irradiation is presented. This method is significantly improved from previously described protocols in terms of applicability of wide ranging aryl aldehydes, better yields, shorter reaction times, facile work up and essentially no need of column chromatography. The photophysical properties of this series of compounds were studied for their possible applicability in the field of metal ion sensors. In solution, two compounds, 2‐(cyclohexylamino)‐3‐(1 H ‐indol‐3‐yl)‐6,6‐dimethyl‐6,7‐dihydrobenzofuran‐4(5 H )‐one ( 1 i ) and 2‐( tert ‐butylamino)‐3‐(1 H ‐indol‐3‐yl)‐6,6‐dimethyl‐6,7‐dihydrobenzofuran‐4(5 H )‐one ( 1 j ), underwent an observable color change from yellow to colorless in the presence of aluminum(III) ions. Further studies to investigate the UV absorption and luminescence behavior of these compounds revealed their utility as “naked‐eye sensors” for aluminum detection.