149139-38-8Relevant academic research and scientific papers
Reactivity of 1-(2-nitrophenyl)-5-aminopyrazoles under basic conditions and synthesis of new 3-, 7-, and 8-substituted pyrazolo [5,1-c][1,2,4]benzotriazine 5-oxides, as benzodiazepine receptor ligands
Costanzo,Guerrini,Bruni,Selleri
, p. 1369 - 1376 (2007/10/02)
The reaction of 1-(2-nitrophenyl)-5-aminopyrazoles under basic conditions has been reinvestigated and the structures of the obtained pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides confirmed by spectroscopic means. In particular the different aromatic nucleophilic attack on 8-chloro derivatives 4a and 6a and 7-nitro derivatives 11a and 12a was determined. From these latter compounds unexpected (phenyl-ONN-azoxy)pyrazoles were isolated.
Cyanoacetaldehyde - New Synthetic Applications of an Old Compound Syntheses with Nitriles, XCI
Jachak, Madhukar,Kriessmann, Ulrike,Mittelbach, Martin,Junek, Hans
, p. 199 - 208 (2007/10/02)
Various reactions of cyanoacetaldehyde (1), freshly prepared by ozonization of (E)-1,4-dicyano-2-butene or allylcyanide, are described.Thus, conversion of 1 with anilines gave β-phenylaminoacrylonitriles 2a-e.Reaction of 1 with hydrazines led to the corresponding hydrazones 3a-e, which could be cyclized under alkaline conditions to 5-aminopyrazoles 4a-d.An aldol-type condensation product 5a could be obtained by reaction of 1 with sodiumphenoxide.Treatment of 1 with dimethylformamide-dimethylacetal led to the formation of (E)-3-dimethylamino-2-formylpropenenitrile (6), a very useful synthon in synthetic chemistry.For the determination of the structure of 6 the method of steady state diffferential NOEs was used.Reaction of 6 with hydrazines gave 1-substituted-4-cyanopyrazoles 7a-k. Keywords.Cyanoacetaldehyde; Hydrazones; Cyanopyrazoles; Aminopyrazoles.
