synthesis of 4-amino-4,5-dihydro-1h-1,2,4-triazole-5-ones and their isatin-3-imine derivatives合成4-amino-4 5-dihydro-1h-1 2,4-triazole-5-ones及其isatin-3-imine衍生品.pdf

Molecules 2005, 10, 376-382 molecules ISSN 1420-3049 Synthesis of 4-Amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their Isatin-3-imine Derivatives Bahittin Kahveci Department of Chemistry, Rize Faculty of Arts and Science, Karadeniz Technical University, 53100, Rize, Turkey. * Author to whom correspondence should be addressed; e-mail: bahittin@ Received: 12 July 2004 / Accepted: 1 September 2004 / Published: 28 February 2005 Abstract: Iminoester hydrochlorides 1 have been synthesized. These compounds were then converted into ester ethoxycarbonyl hydrazones 2, from which in turn a new series of substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones, 3, was then prepared. Finally a set of isatin imine derivatives 4 was obtained from the reaction of compounds 3 with isatin. The structures of all the new synthesized compounds were confirmed by elemental analyses, IR, 1H-NMR and 13C-NMR spectra. Keywords: Iminoesters; ethoxycarbonyl hydrazones; 4-amino-1,2,4-triazole-5-ones; isatin Introduction The synthesis and antibacterial activity of some 4-amino-4,5-dihydro-1H-1,2,4-triazoles and their derivatives have been reported in the literature [1-5]. A number of studies involving the antibacterial and antitumor activity of some 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their derivatives have also been published recently [6-14]. There are also many studies on isatin (1H-indole-2,3-dione) in the literature. The synthetic versatility of isatin has led to the exten