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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.


Mechanochemical reaction using 4-nitrobenzaldehyde (3 a) as a substrate. Reagents and conditions: a) no solvent, grinding, 30 min, rt, 83 %.
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sch01: Mechanochemical reaction using 4-nitrobenzaldehyde (3 a) as a substrate. Reagents and conditions: a) no solvent, grinding, 30 min, rt, 83 %.

Mentions: With our focus on environmentally benign chemistry, initially we ground dimedone 2 a, 4-nitrobenzaldehyde 3 a and tert-butylisonitrile 4 a together without any solvent for 30 min at room temperature (Scheme 1). Interestingly, product 1 a was deposited as a red solid in 83 % yield. This is the first report of such a facile synthesis of 1 a by mechanochemical route. It is worth noting that the same product was obtained in lower yields by Shaabani et al. using conventional heating/prolonged reaction times.19 When the aryl aldehyde was changed from 3 a to unsubstituted benzaldehyde 3 b, the yield of the corresponding product 1 b was just 15 %, with most of the dimedone starting material remaining unreacted (Table 1, entry 1).


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)

Mechanochemical reaction using 4-nitrobenzaldehyde (3 a) as a substrate. Reagents and conditions: a) no solvent, grinding, 30 min, rt, 83 %.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

sch01: Mechanochemical reaction using 4-nitrobenzaldehyde (3 a) as a substrate. Reagents and conditions: a) no solvent, grinding, 30 min, rt, 83 %.
Mentions: With our focus on environmentally benign chemistry, initially we ground dimedone 2 a, 4-nitrobenzaldehyde 3 a and tert-butylisonitrile 4 a together without any solvent for 30 min at room temperature (Scheme 1). Interestingly, product 1 a was deposited as a red solid in 83 % yield. This is the first report of such a facile synthesis of 1 a by mechanochemical route. It is worth noting that the same product was obtained in lower yields by Shaabani et al. using conventional heating/prolonged reaction times.19 When the aryl aldehyde was changed from 3 a to unsubstituted benzaldehyde 3 b, the yield of the corresponding product 1 b was just 15 %, with most of the dimedone starting material remaining unreacted (Table 1, entry 1).

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.