التفاصيل البيبلوغرافية
| العنوان: |
Synthesis and Reactivity of 4-(2-Chloro-5-nitrophenyl)- 1,2,3-thiadiazole. A Novel One-pot Synthesis of N-Substituted Indole-2-thiols. |
| المؤلفون: |
Androsov, Dmitry A.1, Neckers, Douglas C.1 neckers@photo.bgsu.edu |
| المصدر: |
Journal of Organic Chemistry. 7/6/2007, Vol. 72 Issue 14, p5368-5373. 6p. 5 Diagrams, 2 Charts. |
| مصطلحات موضوعية: |
*PYRROLES, *ORGANOCHLORINE compounds, *ORGANIC synthesis, *THIOLS, *ACETIC acid |
| مستخلص: |
4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole undergoes ring opening to produce a thioketene intermediate that reacts with an O- or N-nucleophile, forming an ester or an amide of the aryl-substituted thioacetic acid. Intermolecular cyclization of the thioacetic acid derivative via nucleophilic substitution of halogen in the aromatic ring gives an N-substituted indole-2-thiol (in case of an N-nucleophile) or a 2-alkoxy-substituted benzo[b]thiophene (in case of an O-nucleophile). The reaction is also applicable to the synthesis of heterocyclic analogues of N-substituted indole-2-thiols: 1-butyl-1,3-dihydropyrrolo[2,3-b]pyridine-2-thione was synthesized as an example. In the presence of potassium thioacetate (an S-nucleophile) 4-nitro-2-(1,2,3-thiadiazol-4-yl)benzenethiol is formed more quickly than thiadiazole ring opening occurs, making the heterocyclic ring tolerant toward the base. [ABSTRACT FROM AUTHOR] |
| قاعدة البيانات: |
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