Oxoisoindolium hexachloroantimonate 1a was reacted with different nitriles to afford 2-azoniaallene salts. These underwent cyclization on heating, furnishing tetracyclic compounds 2a, b. Oxoisoindolo[2,1-a]quinazolinium hexachloroantimonate 3 reacted with p-toluidine to afford the corresponding salt 4. This was neutralized with sodium carbonate to give the corresponding free base 5. Isoindolo[2,1-a]quinazoline derivative 6 was prepared by treatment of 3 with benzohydrazide in dichloroethane. Reaction of the extremely sensitive salt of oxoisoindolium 1 with aminothiazole derivative 7 afforded the formal salts of 2-azoniaallene 8. Neutralization of these afforded the corresponding free base 9. The structures of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, and mass spectroscopy. The free base compounds were screened for antimicrobial activity.
Research on Chemical Intermediates – Springer Journals
Published: Sep 3, 2013
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