674289-75-9Relevant academic research and scientific papers
A facile carbene route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides
Novikov, Mikhail S.,Khlebnikov, Alexander F.,Shevchenko, Mikhail V.
, p. 177 - 181 (2003)
2-Fluoro-2-pyrrolines have been prepared by a domino reaction of difluorocarbene with N-substituted ketimines in the presence of fumaronitrile, malenitrile or dimethyl maleate, involving azomethine ylide formation, 1,3-dipolar cycloaddition, and dehydrofluorination. The reactions of 1H-dibenzo[b,e] azepine and 3,4-dihydroisoquinolines with difluorocarbene in the presence of fumaronitrile proceed with the formation of fluorinated 1H-dibenzo[c,f] pyrrolo[1,2-a]azepine and pyrrolo[2,1-a]isoquinoline derivatives. The yields of 2-fluoro-2-pyrrolines depend mostly on their resistance to chromatographic work-up and are higher for 5,5-disubstituted pyrrolines compared to 5-monosubstituted derivatives.
1,3-Dipolar cycloaddition of difluoro-substituted azomethine ylides. Synthesis and transformations of 2-fluoro-4,5-dihydropyrroles
Novikov,Khlebnikov,Shevchenko,Kostikov,Vidovic
, p. 1496 - 1506 (2007/10/03)
2-Fluoro-4,5-dihydropyrrole-3,4-dicarboxylic acid derivatives were obtained by reaction of difluorocarbene with N-substituted ketone imines in the presence of fumaronitrile, maleonitrile, or dimethyl maleate. The reaction involves intermediate formation of azomethine ylides and their subsequent cycloaddition at the double bond. 11H-Dibenz[b,e]azepine and 3,4-dihydroisoquinolines react with difluorocarbene in the presence of fumaronitrile to give fluoro-substituted dibenzo[c,f]pyrrolo[1,2-a]azepine and pyrrolo[2,1-a]-isoquinoline derivatives. Treatment of 2-fluoro-4,5-dihydropyrrole-3,4-dicarbonitrile with amines and alkoxides affords the corresponding 2-amino- and 2-alkoxy derivatives, while its reactions with hydrazine hydrate and benzimidamide lead to formation of substituted pyrrolo[2,3-c]pyrazole and pyrrolo[2,3-d]-pyrimidine derivatives.
