[DABCO-C18]Br: A novel basic surfactant for the synthesis of dihydropyrano[3,2-c]chromenes and 2-aminobenzochromenes under ambient conditions
[Display omitted] •A new [DABCO-C18]Br surfactant showed excellent surfactant properties.•CMC is 1.15 mM as determined by the conductivity method and 1.0 mM by UV–Vis absorption.•It acts as a tertiary base surfactant for the synthesis of dihydropyrano[3,2-c]chromene and 2-aminobenzochromenes.•This p...
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Veröffentlicht in: | Journal of molecular liquids 2023-12, Vol.391, p.123247, Article 123247 |
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•A new [DABCO-C18]Br surfactant showed excellent surfactant properties.•CMC is 1.15 mM as determined by the conductivity method and 1.0 mM by UV–Vis absorption.•It acts as a tertiary base surfactant for the synthesis of dihydropyrano[3,2-c]chromene and 2-aminobenzochromenes.•This protocol is fast, energy-efficient.•It boasts impressive environmentally-friendly credentials.
We successfully produced a new surfactant called [DABCO-C18]Br, which is a monoquaternized octadecyl-1,4-diazabicyclo[2.2.2]octane bromide. The yield was good. The surfactant that was created was analyzed using techniques such as 1H NMR, 13CNMR, and Mass characterization. We analyzed the synthesized [DABCO-C18]Br salt and found that it has great surfactant properties. Its critical micelle concentration (CMC) is 1.15 mM as determined by the conductivity method and 1.0 mM by UV–Vis absorption measurement at 298.15 K. The values align well with the critical micelle concentration (CMC) of the commonly used surfactant [C16TAB]. We have studied the catalytic efficiency of [DABCO-C18]Br, a tertiary base surfactant, for the synthesis of dihydropyrano[3,2-c]chromenes. This synthesis is achieved through one-pot three-component reactions involving aromatic aldehydes, malononitrile, and 4-hydroxycoumarin in water at room temperature. The method was also extended for the synthesis of 2-aminobenzochromenes via one-pot three-component reactions of aromatic aldehydes, malononitrile, and lawsone in water at 80 °C. The products were achieved in yields ranging from good to excellent within a timeframe of 30–60 min. In addition, the aqueous solution with [DABCO-C18]Br was reused up to four times with a minor reduction in product output. This protocol is fast, energy-efficient, and can be used on a large scale for synthetic purposes. Additionally, it boasts impressive environmentally-friendly credentials. |
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ISSN: | 0167-7322 |
DOI: | 10.1016/j.molliq.2023.123247 |