synthesis of thiadiazoles and 1,2,4-triazoles derived from cyclopropane dicarboxylic acid合成thiadiazoles和1、2、4-triazoles来自环丙烷二羧酸.pdf

Molecules 2005, 10, 1153-1160 molecules ISSN 1420-3049 Synthesis of Thiadiazoles and 1,2,4-Triazoles Derived from Cyclopropane Dicarboxylic Acid . A. Hussain K. Sharba*, Rida H.Al-Bayati , Nadjet Rezki and Mohammed R. Aouad Department of Chemistry, College of Science, Al-Mustansirya University, Baghdad, Iraq. * Author to whom correspondence should be addressed; e-mail: hussainirk@ Received: 29 June 2005; in revised form: 29 August 2005 / Accepted: 30 August 2005 / Published: 30 September 2005 Abstract: New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl) cyclo- propane (7) by ring closure in an alkaline medium. The thiadiazole 2 and the triazole 7 were converted into a variety of derivatives. Keywords: Bis-thiadiazolylcyclopropane, bis–triazolylcyclopropane, azomethines, Mannich bases. Introduction Thiadiazoles, oxadiazoles and triazoles are five–membered rings associated with diverse biological and pharmacological properties [1]. For example, triazole derivatives are active as antibacterial, antiviral and insecticidal agents [2]. Substituted 1,2,4-triazoles have been associated with activities such as anti-inflammatory