2008
DOI: 10.1139/v08-026
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Reaction on a solid surface — A simple, economical, and efficient Mannich reaction of azacrown ethers over graphite

Abstract: Graphite brings about a rapid Mannich reaction with a range of activated and unactivated phenolic compounds such as p-cresol and p-nitrophenol. The reactions are carried out with azacrown ether and paraformaldehyde in solvent-free conditions at 100 °C for 20–30 min. The graphite powder can be reused up to three times after simple washing with acetone.Key words: azacrown ether, lariat ether, graphite, solvent-free, Mannich reaction.

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Cited by 23 publications
(7 citation statements)
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“…We next screened CaO and graphite for Mannich reaction of azacrown ether 3 under similar conditions. We found the yields were further improved to 12-25% and graphite is better than CaO (entries 2, 3,5,6,8,9). In another study to increase the yield, experiments were done under solven-free condition in the presence of CaO and graphite.…”
Section: Resultsmentioning
confidence: 93%
See 1 more Smart Citation
“…We next screened CaO and graphite for Mannich reaction of azacrown ether 3 under similar conditions. We found the yields were further improved to 12-25% and graphite is better than CaO (entries 2, 3,5,6,8,9). In another study to increase the yield, experiments were done under solven-free condition in the presence of CaO and graphite.…”
Section: Resultsmentioning
confidence: 93%
“…We have previously shown that new lariat ethers can be prepared by the reaction of azacrown ether 3, phenols and paraformaldehyde on solid supported (CaO and graphite) [5,6]. In continuation of our interest in Mannich base synthesis, in peculiar on solid supports, we now described new method to the aminoalkylation of polycyclic and heterocyclic aromatic compounds.…”
Section: Introductionmentioning
confidence: 99%
“…This simplified reaction has received a growing attention from industrial research groups. “Mannich” reactions are among the most important one‐pot multicomponent reactions for the formation of the carbon–carbon bond . The resultant products acquired from “Mannich” reactions are important as synthetic versatile intermediates, natural products, and biologically active compounds .…”
Section: Introductionmentioning
confidence: 99%
“…Synthetic organic routes followed by using heterogeneous catalysts have advantages over their counterparts in which, used-catalyst can be easily recycled [21]. As a part of our continued efforts to utilize heterogeneous catalysts for developing organic reactions [37][38][39][40][41][42][43][44][45][46][47][48][49][50], herein we report on a new and reused catalyst system based on copper on charcoal (Cu/C). This heterogeneous catalyst system exhibits an excellent catalytic performance for the construction of the 2-arylbenzimidazoles framework.…”
Section: Introductionmentioning
confidence: 99%