52353-62-5Relevant articles and documents
Syntheses of α-Haloformylarylhydrazines and Their Self-dimerizations
Kuo, C. N.,Wu, M. H.,Chen, S. P.,Li, T. P.,Huang, C. Y.,Yeh, M. Y.
, p. 849 - 856 (2007/10/03)
α-Haloformylarylhydrazine hydrohalides 1 were prepared through ring opening of 3-aryl-4-halosydnones 7 with hydrohalic acids in EtOAc in moderate yields.Reactions between compounds 1 and primary alcohols gave alkyl 1-arylhydrazinecarboxylates 12 and 14, important intermediates in syntheses of antiinflammatory drugs.Compounds, 16, 4-aryl-2-(arylhydrazin-1-yl)-1,3,4-oxadiazolin-5-ones, and compounds 18, 1,4-diaryl-1,4-dihydro-1,2,4,5-tetrazine-3,6-(2H,5H)-diones, were synthesized by self-dimerization of compounds 1.Compounds 18 were also converted to compounds 17 via intramolecular rearrangement.Structural elucidation and verification of the reaction mechanisms are presented.Key Words 3-Aryl-4-halosydnone; α-Haloformylarylhydrazine hydrohalide; Acid hydrolysis; Self-dimerization; Intramolecular rearrangement.