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

Kumar M, Kumawat LK, Gupta VK, Sharma A - ChemistryOpen (2015)

Bottom Line: As such, improved synthetic access to furans is an important research goal.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.Further studies to investigate the UV absorption and luminescence behavior of these compounds revealed their utility as "naked-eye sensors" for aluminum detection.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Indian Institute of Technology Roorkee Roorkee, Uttarakhand, 247667, India.

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.

No MeSH data available.


Examples of natural and unnatural annulated furans reported in the literature that exhibit a wide range of activities. Compound A is an example of a photosensitive polyfuran, and compound B is a known anticancer hit (EC50=40 ng mL−1).
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fig01: Examples of natural and unnatural annulated furans reported in the literature that exhibit a wide range of activities. Compound A is an example of a photosensitive polyfuran, and compound B is a known anticancer hit (EC50=40 ng mL−1).

Mentions: Among oxygenated heterocycles, fused and substituted furan analogues form a class compounds worthy of considerable attention. They are the basic scaffolds of a myriad of natural products and possess a wide spectrum of medicinal activities.1–3 Some of the annulated and polymeric furans show outstanding photosensitivity4 and are important in the field of conducting polymers,5 materials science,5 photovoltaics,6 and photo-chemotherapeutics4 (Figure 1). Considering their wide-spread utility, synthetic advancement toward annulated furans and related structures, and assessment of their absorption- and fluorescence-based metal-sensing abilities are important research goals. This selective sensing/signaling of ecologically and biologically important metal ions is a fascinating and emerging area of research because of its simplicity, improved selectivity, real-time detection, portability and non-destructive nature.7–9


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

Kumar M, Kumawat LK, Gupta VK, Sharma A - ChemistryOpen (2015)

Examples of natural and unnatural annulated furans reported in the literature that exhibit a wide range of activities. Compound A is an example of a photosensitive polyfuran, and compound B is a known anticancer hit (EC50=40 ng mL−1).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4608531&req=5

fig01: Examples of natural and unnatural annulated furans reported in the literature that exhibit a wide range of activities. Compound A is an example of a photosensitive polyfuran, and compound B is a known anticancer hit (EC50=40 ng mL−1).
Mentions: Among oxygenated heterocycles, fused and substituted furan analogues form a class compounds worthy of considerable attention. They are the basic scaffolds of a myriad of natural products and possess a wide spectrum of medicinal activities.1–3 Some of the annulated and polymeric furans show outstanding photosensitivity4 and are important in the field of conducting polymers,5 materials science,5 photovoltaics,6 and photo-chemotherapeutics4 (Figure 1). Considering their wide-spread utility, synthetic advancement toward annulated furans and related structures, and assessment of their absorption- and fluorescence-based metal-sensing abilities are important research goals. This selective sensing/signaling of ecologically and biologically important metal ions is a fascinating and emerging area of research because of its simplicity, improved selectivity, real-time detection, portability and non-destructive nature.7–9

Bottom Line: As such, improved synthetic access to furans is an important research goal.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.Further studies to investigate the UV absorption and luminescence behavior of these compounds revealed their utility as "naked-eye sensors" for aluminum detection.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Indian Institute of Technology Roorkee Roorkee, Uttarakhand, 247667, India.

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.

No MeSH data available.