81585-45-7Relevant academic research and scientific papers
A STUDY OF THE EFFECT OF NITRO GROUP IN THE SYNTHESIS OF PYRAZOLES AND THIADIAZOLINES FROM HYDRAZIDOYL HALIDES.
Hassaneen, Hamdi Mahmoud,Abdelhamid, Abdou Osman,Shawali, Ahmad Sami,Pagni, Richard
, p. 319 - 326 (2007/10/02)
The reaction of C-acetyl-N-(2-nitrophenyl)hydrazidoyl chloride 5 with sodium ethoxide and ethyl cyanoacetate yields only one isolable product identified as ethyl 1-(2-nitrophenyl)-3-acetyl-5-aminopyrazole-4-carboxylate 6, in contrast to the C-phenyl-N-(2-nitrophenyl)hydrazidoyl bromide analog 1.The nitrilimine derived from 5 adds to the C=C double bond of the enol tautomers of acetylacetone and dibenzoylmethane and gives the corresponding pyrazole derivatives 7 and 8, which upon hydrazinolysis yield 11 and 12, respectively.These results indicate that the ortho nitro group in 5 seems to have no influence on the course of the reactions of 5 with dipolarophilic reagents.Nucleophilic substitution of the halogen atom in 5 by thiocyanate anion and morpholine seems to proceed in a normal way as other hydrazidoyl halides to give the corresponding thiadiazoline and amidrazone derivatives 13 and 19 respectively.
