Synthesis of new calix[4]pyrrole derivatives via 1,3-dipolar cycloadditions |
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Authors: | Andreia SF Farinha José AS Cavaleiro |
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Institution: | Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal |
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Abstract: | Octamethylcalix4]pyrrole-2-carbaldehyde 1 and 3-(octamethylcalix4]pyrrol-2-yl)propenal 5 were used as precursors of azomethine ylides, which were trapped in situ with a range of dipolarophiles, such as 1,4-benzoquinone, 1,4-naphthoquinone, and fumaronitrile. Aldehyde 1 showed very low reactivity but the azomethine ylide generated from the reaction of aldehyde 5 with N-methylglycine could be trapped with those dipolarophiles to afford new β-substituted octamethylcalix4]pyrrole derivatives in moderate yields. The resulting cycloadducts show high affinity constants for fluoride and acetate anions; compounds 7 and 8 display sharp changes in color in the presence of these anions. |
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Keywords: | Calixpyrroles 1 3-Dipolar cycloadditions Anion sensors Chromogenic sensors |
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