82453-79-0Relevant academic research and scientific papers
Aza-enamines, VIII. - Electrophilic Substitution reactions at the Azomethine C-Atom of Aldehyde Dialkylhydrazones: Vilsmeier Formylation and Consecutive Reactions
Brehme, Rainer
, p. 2039 - 2046 (2007/10/02)
The reaction of hydrazones 1 with the Vilsmeier reagent yields 3-phenyl-1,4,5-triaza-1,3-pentadienium salts according to their aza-enamine character.Hydrolysis of 2 gives 1-phenylglyoxal 1-dialkylhydrazones 3, which rearrange in acidic media to 1-phenylglyoxal 2-dialkylhydrazones 4.Compound 3h forms the dihydropyrroloimidazole 5 in boiling ethanol.Pyrrolotriazinium salt 6 is obtained by the reaction of 1b with the isolated Vilsmeier reagent from dimethylformamide/oxalyl chloride.
ENAMIN-ANALOGE REAKTIONEN VON ALDEHYD-N,N-DIMETHYLHYDRAZONEN.
Brehme, Rainer,Nikolajewski, Hans-Edmund
, p. 1131 - 1134 (2007/10/02)
Aldehyde-N,N-dimethylhydrazones are regarded as aza-analogous enamines.Accordingly they are substituted on the azomethynecarbon by the electrophilic sulphonylisocyanates and the Vilsmeier-reagent giving the compounds 4 and 6, respectively.
