Synthesis and reactivity of benzothiazol-2-ylcarbonylhydroximoyl chloride, a versatile synthon
โ Scribed by Ahmad M. Farag; Kamal M. Dawood; Abdou O. Abdelhamid
- Book ID
- 104208233
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 386 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
The versatile, hitherto unreported benzothiazol-2-ylcarbonylhydroximoyl chloride (2) was prepared by treatment of the corresponding sulfonium bromide 1 with sodium nitrite and hydrochloric acid in dioxane. Compound 2 reacts with o-aminothiopbenol and with o-phenylenediamine to afford the new ketones 3 and 4, respectively. Oxidation of the latter with lead tetraacetate gave the benzotriazine derivative 7. Reaction of 2 with heterocyclic amines furnished the novel fused heterocycles 8, 9, 12, 14 and 16. Compound 2 reacted also with 2-methyhhiobenzimidazole and gave the new heterocyclic system 18. Treatment of 2 with acrylonitrile, acrylamide and cx-(benzothiazol-2-yl)cinnamonitrile (25) in the presence of triethylamine afforded the isoxazole derivatives 21, 23 and 27, respectively.
๐ SIMILAR VOLUMES
The novel, highly versatile 2-(benzothiazol-2-yl)-1bromo-1,2-ethanedione-1-arylhydrazones 3 were prepared and their behavior toward some nucleophiles was investigated. Thus, reaction of 3 with the sodium salt of malononitrile afforded the aminopyrazolecarbonitriles 5 that undergo cyclocondensation w
The reaction of 3-(benzothiazol-2-yl)-3oxopropanenitrile 1 with active methylene reagents 2a-d and sulfur afforded polysubstituted thiophenes 3a-c . The synthetic potential of the b-enaminonitrile moiety in 3a was explored. The reaction of 3a with active methylene reagents 2a-e afforded thieno [2,3b