ISSN:
0009-2940
Keywords:
Aza-enamines
;
Hydrazones
;
Triazapentadienium salts
;
Phenylglyoxal monohydrazones
;
Pyrrolo[2,1-b]imidazoles
;
Pyrrolo[1,2-b][1,2,4]triazinium salts
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Aza-enamines, VIII. - Electrophilic Substitution Reactions at the Azomethine C-Atom of Aldehyde Dialkylhydrazones: Vilsmeier Formylation and Consecutive ReactionsThe 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.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901231015
Permalink