100873-73-2Relevant articles and documents
SYNTHESIS, CRYSTAL STRUCTURE, AND CONFORMATION OF N-ISONICOTINOYLPHTHALIMIDE
Arinova, A. E.,Fazylov, S. D.,Makhmutova, A. S.,Nurkenov, O. A.,Seilkhanov, T. M.,Turdybekov, D. M.,Turdybekov, K. M.
, p. 1279 - 1284 (2021/09/22)
Abstract: The reaction of phthalic acid anhydride with isonicotinoylhydrazide is carried out under severe conditions with the formation of cyclic phthalic acid imide N-isonicotinoylphthalimide. The structure of the compound is determined by 1H and 13C NMR spectroscopy and from the data of two-dimensional (1H–1H) COSY and (1H–13C) HMQC spectra. The spatial structure and conformation of N-isonicotinoylphthalimide is investigated by single crystal XRD and a semi-empirical quantum chemical method. It is found that π-conjugation between the phenyl and carbonyl groups is practically absent in the free N-isonicotinoylphthalimide molecule and a rotation of the pyridine ring relative to the amide group in the crystal is determined by the π–π interaction between the pyridine rings.
New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol
Brosse, Nicolas,Pinto, Maria-Fatima,Jamart-Gregoire, Brigitte
, p. 4370 - 4374 (2007/10/03)
N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pKa values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.