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The condensation of binucleophilic 3-amino-1-arylimino-1H-isoindoles with bifunctional 1-chloro-benzylisocyanates occurs regioselectively resulting in 3,4-dihydro-1,3,5-triazino[2,1-a]isoindol-2-one derivatives. The structures of the synthesized compounds were unambiguously established by NOE experiments.

The condensation of binucleophilic 3-amino-1-arylimino-1H-isoindoles with bifunctional 1-chloro-benzylisocyanates occurs regioselectively resulting in 3,4-dihydro-1,3,5-triazino[2,1-a]isoindol-2-one derivatives. The structures of the synthesized compounds were unambiguously established by NOE experiments.

A series of N′-(3-amino-1H-isoindol-1-ylidene)alkyl(aryl,heteroaryl)carbohydrazides have been synthesized in good yields and their structure and conformational behavior in the solid state and in solution have been studied by X-ray crystallography, NMR spectroscopy, and quantum calculations. (E)/(Z) amide-type isomerism and the dependence of the isomeric ratio upon steric effects and solvent polarity are discussed. The thermodynamic parameters of (E) (Z) isomerization were determined by 1H NMR dynamic spectroscopy. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)