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Synthesis of Schiff and Mannich Bases of Isatin Derivatives with 4-Amino-4,5-Dihydro-1H-1,2,4-Triazole-5-Ones
Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey
Department of Chemistry, Giresun University, 28049 Giresun, Turkey
* Author to whom correspondence should be addressed.
Received: 15 August 2008; in revised form: 28 August 2008 / Accepted: 1 September 2008 / Published: 10 September 2008
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, 1H- and 13C-NMR data and by elemental analysis.
Keywords: Ethyl imidate hydrochloride; ethoxycarbonyl hydrazones; 4-amino-1; 2; 4- triazole-5-one; isatin; Schiff bases; Mannich bases
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Bekircan, O.; Bektas, H. Synthesis of Schiff and Mannich Bases of Isatin Derivatives with 4-Amino-4,5-Dihydro-1H-1,2,4-Triazole-5-Ones. Molecules 2008, 13, 2126-2135.
Bekircan O, Bektas H. Synthesis of Schiff and Mannich Bases of Isatin Derivatives with 4-Amino-4,5-Dihydro-1H-1,2,4-Triazole-5-Ones. Molecules. 2008; 13(9):2126-2135.
Bekircan, Olcay; Bektas, Hakan. 2008. "Synthesis of Schiff and Mannich Bases of Isatin Derivatives with 4-Amino-4,5-Dihydro-1H-1,2,4-Triazole-5-Ones." Molecules 13, no. 9: 2126-2135.