2‐(Alkylamino)‐3‐aryl‐6,7‐dihydrobenzofuran‐4(5H)‐ones: Improved Synthesis and their Photophysical Properties

ChemistryOpen

Manoj Kumar¹  Lokesh Kumar Kumawat¹  Prof. Vinod Kumar Gupta¹ 

[1] Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand, India

关键词: heterocycles;    isocyanides;    microwave chemistry;    multicomponent reactions;    sensors;   

DOI  :  10.1002/open.201500067

来源: Wiley

【 摘 要 】

Abstract

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-(1H-indol-3-yl)-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-one (1 i) and 2-(tert-butylamino)-3-(1H-indol-3-yl)-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-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.

【 授权许可】

CC BY-NC-ND   
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.