37035-03-3Relevant academic research and scientific papers
gem-cyclodialkylation A facile synthetic route to N-substituted heterocycles
Hargis, Duane C.,Shubkin, Ronald L.
, p. 2991 - 2994 (1990)
N-alkylated and N-arylated pyrroles, pyrrolidines, and piperidines are synthesized in high yield by the reaction between cyclic ethers and primary amines over a heterogeneous titania catalyst.
Cyclodextrin-based PNN supramolecular assemblies: a new class of pincer-type ligands for aqueous organometallic catalysis
Menuel,Bertaut,Monflier,Hapiot
, p. 13504 - 13512 (2015/08/03)
Water-soluble cyclodextrins (CDs) bearing two nitrogen atoms as metal coordinating sites have been synthesized. An appropriate phosphane could be included within their cavity through the primary face to form self-assembled PNN supramolecular edifices. Once the PNN ligands were coordinated to platinum, the resulting complexes proved to be very effective as catalysts in a domino reaction, where a Pt-catalyzed reduction of nitrobenzene was followed by a Paal-Knorr pyrrole reaction. In the nitrobenzene reduction, the modified CDs acted both as first- and second-sphere ligands. Contrary to an acyclic glucopyranose-based NN ligand unable to interact with a phosphane ligand, the CD-based PNN ligands stabilized the catalytic species in water by supramolecular means. Interestingly, the product and the water-soluble Pt-catalyst could be recovered in two different phases once the reaction was complete.
DIASTEREOSELECTIVE ELECTROCHEMICAL REDUCTIVE AMINATION OF 2,5-HEXANEDIONE AND 2,6-HEPTANEDIONE
Concialini, Vittorio,Roffia, Sergio,Savoia, Diego
, p. 77 - 82 (2007/10/02)
The electrochemical reductive amination of 2,5-hexanedione with ammonia and 1-phenylethylamine at the mercury cathode afforded the corresponding 2,5-dimethylpyrrolidines with satisfactory yield and excellent cis-selectivity (90-98percent), but with arylamines mixtures of pyrroles and diastereoisomeric pyrrolidines were obtained.Only pyrroles were obtained with methyl- and benzylamine.On the other hand, 2,6-dimethylpiperidine (98percent cis) was obtained in low yield from 2,6-heptanedione and ammonia.The stereochemical outcome, along with the observation of a single reduction peak for the overall four-electron reduction, is consistent with a mechanism involving reduction of iminium ions, where the diastereoselctivity is controlled in the protonation of cyclic α-aminoalkyl radicals at the radical carbon atom.However, an alternative mechanism, involving the reduction of radicals to the corresponding carbanions followed by fast protonation, although less probable, could not be discarded.
Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6- dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6- heptanedione with hydride reagents
Boga,Manescalchi,Savoia
, p. 4709 - 4722 (2007/10/02)
The reductive amination of 2,5-hexanedione and 2,6-heptanedione with ammonia and primary amines in the presence of hydride reagents afforded 2,5- dimethylpyrrolidines and 2,6-dimethylpiperidines with variable diastereoselectivity, as the cis/trans ratio was affected by the size of the ring formed and the steric and electronic properties of the nitrogen substituent. Increasing the bulkiness of the nitrogen substituent, the cis pyrrolidines and the trans-piperidines were obtained with enhanced selectivity.
One-Pot Synthesis of Substituted Pyrrolidines via Aminomercuration-Demercuration of 1,4- and 1,5-Hexadiene
Barluenga, J.,Najera, C.,Yus, M.
, p. 1297 - 1299 (2007/10/02)
The aminomercuratione-demercuration of 1,4- and 1,5-hexadiene yield cis- and trans-2,5-dimethyl-N-arylpyrrolidines via one-pot process.The intermolecular cyclization reaction goes through the corresponding mercurated pyrrolidines; these intermediates were isolated and characterized when the mercuration reaction was completed.The high stereoselectivity observed allows an easy way of synthesis for N-substituted trans-2,5-dimethylpyrrolidines.
