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

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.

An easily accessible optical chemosensor for Cu2+ based on novel imidazoazine framework, its performance characteristics and potential applications

“…In a continuation of our previous work on chemical sensors [54][55][56][57][58][59][60][61][62], we herein report two new furan-2-yl functionalized imidazoazines (or Gröebke product) IA-1 and IA-2 [63,64] for easy, effective and fast detection of Cu 2+ in mixed aqueous phases. Despite its easy synthetic accessibility presence of donor N and O atoms in attached groups and intense fluorescence nature, this molecular system have never been explored for its metal sensing abilities.…”

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

“…Exploiting microwave irradiation, un-catalyst three-component reaction of isocyanide 87, cyclic 1,3-diketones 197 and aryl aldehyde 198 was performed to give 6,7dihydrobenzofuran-4(5H)-one derivatives 199 under solvent-free conditions (Scheme 47) 187 . It is worth noting that using acyclic 1,3-diketones did not furnish the desired products.…”

Optical and electrochemical dual channel sensing of Cu2+ using functionalized furo[2,3-d]pyrimidines-2,4[1H,3H]-diones

“…The same reviewers also pointed out that despite several practical benefits and high explorative value; most of these systems are under-explored. Only a handful of MCR products have been so far tested for their metal sensing abilities and there is a large scope for further investigation [32][33][34].…”

“…Our group has a long standing interest in the discovery and design of new chemical sensors for biologically and ecologically relevant metal ions [32][33][35][36][37][38][39][40][41][42][43][44]. In light of above discussion, we wish to disclose herein two new furopyrimidine-diones (FPys) based molecular systems for easy and effective detection of copper (Cu 2+ ).…”