Synthesis of Schiff and Mannich bases of isatin derivatives with 4-Amino-4,5-dihydro-1H-1,2,4-triazole-5-ones

BEKİRCAN O., BEKTAŞ H.

MOLECULES, vol.13, no.9, pp.2126-2135, 2008 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 13 Issue: 9
  • Publication Date: 2008
  • Doi Number: 10.3390/molecules13092126
  • Journal Name: MOLECULES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2126-2135
  • Keywords: ethyl imidate hydrochloride, ethoxycarbonyl hydrazones, 4-amino-1,2,4-triazole-5-one, isatin, Schiff bases, Mannich bases, ANTIMICROBIAL ACTIVITY, 1,2,4-TRIAZOLE DERIVATIVES, ANTIINFLAMMATORY AGENTS, ANTICONVULSANT ACTIVITY, BIOLOGICAL EVALUATION, ANTIBACTERIAL, CONDENSATION, ANTIFUNGAL, KETONES
  • Karadeniz Technical University Affiliated: Yes

Abstract

Ethyl imidate hydrochlorides 1 were prepared by passing HCl gas through solutions of substituted benzyl cyanides and absolute ethanol. Ethoxycarbonylhydrazones 2 were synthesized from the reaction of compounds 1 with ethyl carbazate. Treatment of 2 with hydrazine hydrate leads to the formation of substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones 3. Isatin and 5-chloroisatin were added to 3 to form Schiff bases 4 and N-Mannich bases 5 of these compounds were synthesized by reacting with formaldehyde and piperidine. Their chemical structures were confirmed by means of IR, H-1- and C-13-NMR data and by elemental analysis.