70631-05-9Relevant articles and documents
Solvent-free, base-free microwave-mediated iridium-catalyzed N-alkylation of amides with alcohols
Apsunde, Tushar D.,Trudell, Mark L.
, p. 230 - 234 (2014)
Solvent-free, base-free microwave-mediated (CpIrCl2) 2-catalyzed conditions for the N-alkylation of amides with alcohols have been developed. A series of primary and secondary alcohols have been shown to produce high yields of N-alkyl arylamides and N-alkyl alkylamides.
Ring opening of pymisyl-protected aziridines with organocuprates
Bornholdt, Jan,Felding, Jakob,Clausen, Rasmus P.,Kristensen, Jesper L.
supporting information; experimental part, p. 12474 - 12480 (2010/12/25)
The pyrimidine-2-sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl-protected 2-methyl-aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment with a thiolate. The versatility of this new nitrogen protecting group is illustrated with a new synthesis of Selegiline, a monoamine oxidase-B inhibitor marketed for the treatment of Parkinson's disease. Easy on'easy off: The pymisyl group is introduced as a new protecting group for the activation of aziridines towards ring opening with organocuprates (see scheme). It is readily removed under very mild conditions with thiolates. The versatility of the approach is illustrated in a new synthesis of Selegiline, a drug marketed for the treatment of Parkinson's disease.
Aziridines. 77: cis-trans pair of a N-benzoylaziridine: Dependence of carbonyl reactivity on nitrogen pyramid
Falkenstein, Reinhard,Stamm, Helmut
, p. 195 - 196 (2007/10/03)
In a multistep process, anthracenide and both 1-benzoyl-2-methyl-3-phenylaziridines 1a form carbanion 4a that abstracts a proton from the solvent THF. The steep N pyramid of cis-1a makes attack of 4a on C=O of cis-1a fast enough to compete with proton abs