615-11-2Relevant articles and documents
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Nielsen
, p. 1230 (1944)
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Synthesis of amides and esters containing furan rings under microwave-assisted conditions
Janczewski, ?ukasz,Zieliński, Dariusz,Kolesińska, Beata
, p. 265 - 280 (2021/03/17)
In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO? or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl) furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furan-dicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.
Synthesis, characterization and catalytic performances of benzimidazolin-2-iminato actinide (IV) complexes in the Tishchenko reactions for symmetrical and unsymmetrical esters
Liu, Heng,Khononov, Maxim,Fridman, Natalia,Tamm, Matthias,Eisen, Moris S.
, p. 123 - 137 (2017/10/25)
A new family of benzimdazolin-2-iminato actinide?(IV) complexes [(Bim7-MeDipp/MeN)An(N(SiMe3)2)3] (An = U (3), Th (4)) and [(Bim4-MeDipp/MeN)An(N(SiMe3)2)3] (An = U (5), Th (6)) were synthesized and their solid state structures were established by single-crystal X-ray diffraction analysis. The catalytic performances of complexes 3–6 towards the homo- and cross-coupling of aldehydes (Tishchenko reaction) were studied and the thorium complexes 4 and 6 displayed moderate to high activities for the production of the corresponding symmetric and unsymmetrical esters. Coupling of aldehyde and alcohols, known as the tandem proton-transfer esterification, and the intermolecular coupling reaction between aldehyde and trifluoromethylketones were also investigated by these thorium complexes, indicating a complementary method to obtain unsymmetrical esters selectively. Plausible mechanisms for these reactions are proposed based on stoichiometric studies.