55110-58-2Relevant academic research and scientific papers
A ring closing metathesis-manganese dioxide oxidation sequence for the synthesis of substituted pyrroles
Keeley, Aaron,McCauley, Shane,Evans, Paul
, p. 2552 - 2559 (2016/04/26)
The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were obtained for a variety of substituents and the procedure may also be conducted in one-pot. 2-Bromo N-sulfonyl adducts prepared in this manner were subjected to an intramolecular Heck-type cyclisation, forming cyclic sulfonamides.
An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis
Sawadjoon, Supaporn,Samec, Joseph S. M.
, p. 2548 - 2554 (2011/05/04)
The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.
Reaction of lithium trimethylsilyldiazo-methane with n,n-dialkylamides of α-keto acids and n,n-disubstituted α-amino ketones
Ogawa, Hideki,Aoyama, Toyohiko,Shioiri, Takayuki
, p. 75 - 82 (2007/10/02)
Lithium trimethylsilyldiazomethane smoothly reacted with N ,N -dialkylamides of α-keto acids and N ,N-disubstituted α-amino ketones to give 2-oxo-3-pyrrolines and 3-pyrrolines, respectively, in good to moderate yields.
