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Molecules 2005, 10(9), 1161-1168; doi:10.3390/10091161
Article

Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene

* , ,  and
Department of Chemistry, College of Science, Al-Mustansirya University, Baghdad, Iraq
* Author to whom correspondence should be addressed.
Received: 29 June 2005 / Revised: 29 August 2005 / Accepted: 30 August 2005 / Published: 30 September 2005
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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 . Benzo[b]thiophene; oxadiazole; thiadiazole; 4H-1; 2; 4-triazole-3-thiol; azomethine; Mannich bases .
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Sharba, A.; Al-Bayati, R.; Aouad, M.; Rezki, N. Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene. Molecules 2005, 10, 1161-1168.

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