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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

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Received: 29 June 2005; in revised form: 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 .
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MDPI and ACS Style

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.

AMA Style

Sharba A, Al-Bayati R, Aouad M, Rezki N. Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene. Molecules. 2005; 10(9):1161-1168.

Chicago/Turabian Style

Sharba, A.; Al-Bayati, R.; Aouad, M.; Rezki, N. 2005. "Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene." Molecules 10, no. 9: 1161-1168.



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