Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiol
ABSTRACT<br /> In this paper the synthesis of some substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole is reported. 3-chloro-4-nitro-2-chloro carbonyl benzo [b] thiophene(1) was synthesized from 2-nitrocinnamic acid by its reaction with thionyl chloride/dimethyl formamide in pyr...
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| Format: | Article |
| Language: | Arabic |
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College of Education for Pure Sciences
2010-12-01
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| Series: | مجلة التربية والعلم |
| Subjects: | |
| Online Access: | https://edusj.mosuljournals.com/article_59245_86086778cb0fd6b0bc0c193b15902990.pdf |
| _version_ | 1819112968397258752 |
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| author | Khalid M. Daoud Amal N. Ali Amina A. Ahmed |
| author_facet | Khalid M. Daoud Amal N. Ali Amina A. Ahmed |
| author_sort | Khalid M. Daoud |
| collection | DOAJ |
| description | ABSTRACT<br /> In this paper the synthesis of some substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole is reported. 3-chloro-4-nitro-2-chloro carbonyl benzo [b] thiophene(1) was synthesized from 2-nitrocinnamic acid by its reaction with thionyl chloride/dimethyl formamide in pyridine. Acid chloride(1) was converted to acid hydrazide(2) by its reaction with hydrazine hydrate in chloroform. The hydrazide (2) was treated with formic acid to give 3-chloro-4-nitro-2-[N-formyl acid hydrazide] benzo [b] thiophene (3), which was converted to substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole (4,5) by its reaction with phosphorus pentoxide and phosphorus pentasulfide respectively. Treatment of acid hydrazide (2) with phenyl isothiocyanate gave substituted thiosemicabazide (6), which cyclized with sodium hydroxide solution to substituted 1,2,4-triazole (7). Compound (1) was treated with thiosemicarbzide in dry benzene to give substituted thiosemicarbazide (8), the substituted thiosemicarbazide (8) was cyclized with sodium hydroxide solution to give 5-substituted 1,2,4-triazole 3-thiol (9), alkylation of 1,2,4- triazole (9) with propyl / butyl chloride in ethanol gave 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-propyl/butyl thiol (10,11) respectively. The structures of the synthesized compounds were confirmed by spectral and physical methods. |
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| format | Article |
| id | doaj.art-d23529aa4287430bb96298ca3cf5912e |
| institution | Directory Open Access Journal |
| issn | 1812-125X 2664-2530 |
| language | Arabic |
| last_indexed | 2024-12-22T04:21:56Z |
| publishDate | 2010-12-01 |
| publisher | College of Education for Pure Sciences |
| record_format | Article |
| series | مجلة التربية والعلم |
| spelling | doaj.art-d23529aa4287430bb96298ca3cf5912e2022-12-21T18:39:15ZaraCollege of Education for Pure Sciencesمجلة التربية والعلم1812-125X2664-25302010-12-01234192610.33899/edusj.2010.5924559245Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiolKhalid M. DaoudAmal N. AliAmina A. AhmedABSTRACT<br /> In this paper the synthesis of some substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole is reported. 3-chloro-4-nitro-2-chloro carbonyl benzo [b] thiophene(1) was synthesized from 2-nitrocinnamic acid by its reaction with thionyl chloride/dimethyl formamide in pyridine. Acid chloride(1) was converted to acid hydrazide(2) by its reaction with hydrazine hydrate in chloroform. The hydrazide (2) was treated with formic acid to give 3-chloro-4-nitro-2-[N-formyl acid hydrazide] benzo [b] thiophene (3), which was converted to substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole (4,5) by its reaction with phosphorus pentoxide and phosphorus pentasulfide respectively. Treatment of acid hydrazide (2) with phenyl isothiocyanate gave substituted thiosemicabazide (6), which cyclized with sodium hydroxide solution to substituted 1,2,4-triazole (7). Compound (1) was treated with thiosemicarbzide in dry benzene to give substituted thiosemicarbazide (8), the substituted thiosemicarbazide (8) was cyclized with sodium hydroxide solution to give 5-substituted 1,2,4-triazole 3-thiol (9), alkylation of 1,2,4- triazole (9) with propyl / butyl chloride in ethanol gave 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-propyl/butyl thiol (10,11) respectively. The structures of the synthesized compounds were confirmed by spectral and physical methods.https://edusj.mosuljournals.com/article_59245_86086778cb0fd6b0bc0c193b15902990.pdf4-oxadiazole34-thiadiazole124-triazole |
| spellingShingle | Khalid M. Daoud Amal N. Ali Amina A. Ahmed Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiol مجلة التربية والعلم 4-oxadiazole 3 4-thiadiazole 1 2 4-triazole |
| title | Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiol |
| title_full | Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiol |
| title_fullStr | Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiol |
| title_full_unstemmed | Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiol |
| title_short | Synthesis of 2-(3-chloro-4-nitro-1-benzothien-2-yl)-1,3,4-oxadiazole-1,3,4-thiadiazole and 5-(3-chloro-4-nitro-1-benzothien-2-yl)-4H-1,2,4-triazole-3-thiol |
| title_sort | synthesis of 2 3 chloro 4 nitro 1 benzothien 2 yl 1 3 4 oxadiazole 1 3 4 thiadiazole and 5 3 chloro 4 nitro 1 benzothien 2 yl 4h 1 2 4 triazole 3 thiol |
| topic | 4-oxadiazole 3 4-thiadiazole 1 2 4-triazole |
| url | https://edusj.mosuljournals.com/article_59245_86086778cb0fd6b0bc0c193b15902990.pdf |
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