synthesis of oxadiazoles, thiadiazoles and triazoles derived from benzo[b]thiophene恶二唑的合成thiadiazoles源于氮杂四唑和苯并[b]噻吩.pdfVIP

Molecules 2005, 10, 1161-1168 molecules ISSN 1420-3049 Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene. A. Hussain K. Sharba *, R. H. Al-Bayati, M. Aouad and N. Rezki 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: In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compound 2 with formic acid gave the N-formyl acid hydrazide 4, which upon refluxing with phosphorous pentoxide or phosphorous pentasulphide in xylene yielded the corresponding 2- (3-chloro-1-benzothien-2-yl)-1,3,4-oxadiazole (5) and 2-(3-chloro-1-benzo-thien-2-yl)-1,3,4- thiadiazole (6). Reaction of 1-thiosemicarbazide 7 with NaOH leads to ring closure giving 5- (3-chloro-1-benzothien-2- yl)-4H–triazole-3-thiol (8) which is converted into a number of derivatives 9-12 Reaction of 2 with phenyl isothiocyanate and NaOH afforded 5-(3-chloro- 1-benzothien-2-yl)-4-(phenyl)-4H-1,2,4-triazole-3-thiol (14). Keywords: Benzo[b]thiophene, oxadiazole, thiadiazole, 4H-1,2,4-triazole-3-thiol, azomethine, Mannich bases . Introduction Derivatives of 1,3,4–oxadiazole and 1,3,4 –thiadiazole have been found to possess a wide sp