2424-05-7Relevant articles and documents
Synthesis and characterization of macrocyclic polyether N,N′-Diallyl-7,16-diaza-1,4,10,13-tetraoxa-dibenzo-18-crown-6
Toeri, Julius,Laborie, Marie-Pierre,McPhee, Derek J.
, (2016)
In this study an efficient and direct production procedure for a macrocyclic polyether N,N′-diallyl-7,16-diaza-1,4,10,13-tetraoxa-dibenzo-18-crown-6 from the reaction of catechol and N, N-bis(2-chloroethyl)prop-2-en-1-amine in n-butanol in the presence of a strong base is reported. The synthesis involves a two-step addition of sodium hydroxide to enhance the cyclization process, and at the end of the reaction, the reaction mixture is neutralized and the solvent replaced with water in-situ through distillation to afford a relatively pure precipitate that is easily recrystallized from acetone. The yield of the macrocycle was 36%-45% and could be scaled-up to one-mole quantities. The structure and purity of this compound was verified on the basis of elemental analysis, IR, UV-Vis,1 H-, 13C-NMR, 2D-NMR, mass spectroscopy, and thermal analysis. The white crystalline compound has a sharp melting point of 124 °C and a crystallization temperature of 81.4 °C determined by differential scanning calorimetry. Our motivation behind the synthesis of the bibracchial lariat azacrown polyether ligand was to examine its possible applications in ion-selective polymer-supported materials.
Synthesis of azacrown ethers modified with side-chains containing germanium
Suzuki, Ryoko,Matsumoto, Takashi,Tanaka, Katsumi,Takeuchi, Yoshito,Taketomi, Tamotsu
, p. 108 - 123 (2007/10/03)
The reaction between ethanolamine (4) and tri- or tetraethylene tosylate (5) and (13) gave 9- and 12-membered monoazacrowns with a -CH2CH2OH residue on nitrogen, A-OH and B-OH, together with 18- and 24-membered diazacrown ethers with the same substituent on nitrogen, E-OH and F-OH. If 2-(2-aminoethoxy)ethanol (12) was used in the reaction described above, instead of 4, the final products, G-OH and H-OH, and K-OH and L-OH, have a longer side chain, -CH2CH2OCH2CH2OH, on nitrogen (Route 1). A series of reactions involving bromoethanol (6) and diethanolamine (9) formed, with 5 or 13, 18- and 24-membered monoazacrowns with the shorter substituent as described above, a 15-membered monoazacrown ether C-OH and an 18-membered D-OH. If 2-(2-chloroethoxy)ethanol (14) is used instead of 6, I-OH and J-OH are obtained (Route 2′). All these hydroxy azacrown ethers were made to react with 3-trimethylgermylpropionic acid (18) to give the corresponding germanium-containing A-L. A preliminary investigation was carried out on the cation transport capability of these germanium-containing azacrown ethers to observe whether germanium might enhance their cation transporting capability.
6-ALLYL-2,2-DIORGANO-1,3-DIOXA-6-AZA-2-SILACYCLOOCTANES
Voronkov, M. G.,Kudyakov, N. M.,Vitkovskii, V. Yu.,Albanov, A. I.,Mirskov, R. G.
, p. 316 - 318 (2007/10/02)
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