synthesis of schiff and mannich bases of isatin derivatives with 4-amino-4,5-dihydro-1h-1,2,4-triazole-5-ones合成的希夫曼尼希碱与4-amino-4靛红衍生物,5-dihydro-1h-1,2,4-triazole-5-ones.pdfVIP
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Molecules 2008, 13, 2126-2135; DOI: 10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/molecules
Article
Synthesis of Schiff and Mannich Bases of Isatin Derivatives with
4-Amino-4,5-Dihydro-1H-1,2,4-Triazole-5-Ones
Olcay Bekircan 1, * and Hakan Bektas 2
1 Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey
2 Department of Chemistry, Giresun University, 28049 Giresun, Turkey; E-mail:
hakanbektas@.tr
* Author to whom correspondence should be addressed; E-mail: obekircan@.
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.
Introduction
Schiff bases are
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