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Aromatic and Heterocyclic Derivatives of Isoindoline

Heterocyclic compounds containing isoindoline skeletons have been found interesting due to their presence in number of natural and synthetic bioactive compounds. Some examples of such compounds are staurosporine (protein kinase C inhibitor), idoprofen (anti-inflammatory agent) and pazinaclone (anxiolytic agent)1, 2. This report describes synthesis of imino derivatives of isoindoline as potentially biologically active compounds. 1:2 condensation of o-phthalaldehyde and primary aromatic and heterocyclic amines in absolute ethanol at room temperature gave desired 1-aril-imino-2-aril-isoindolines. Compounds 1 and 2 were prepared from amino-phenyl derivatives and compounds 3 and 4 were prepared from amino-pyridyl derivatives. Compound 5 was prepared from 2-amino-benzimidazole and compound 6 was prepared from 2-amino-benzothiazole. All compounds are characterized by 1H and 13C NMR spectroscopy. Furthermore structures of compounds 2, 3 and 4 are confirmed by X-ray diffraction on monocrystal. References [1] Takahashi, I. ; Hatanaka, M. ; Heterocycles 45 (1997) 2475-2499. [2] Kundu, N. G. ; Khan, M. W. ; Mukhopadhyay, R. ; J. Indian Chem. Soc. 78 (2001) 671. [3] Takahashi, I. ; Miyamoto, R. ; Nishiuchi, K. ; Hatanaka, M. ; Yamano, A. ; Sakushima, A. ; Hosoi, S. ; Heterocycles 63 (2004) 1267-1271.

isoindoline; heterocycles

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