On Water: Metal-Free Synthesis of Highly Functionalized Benzothiazolylidene from ortho-Haloanilines
| Autor: | Kapil Mohan Saini, Akhilesh K. Verma, Shiv Kumar, Rakesh K. Saunthwal |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Organic Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Thiourea Nucleophilic aromatic substitution Intramolecular force Michael reaction Nucleophilic substitution Benzamide Thiazole Triethylamine |
| Zdroj: | The Journal of Organic Chemistry. 84:2689-2698 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | An environmentally benign, transition-metal-free organic base promoted one-pot cascade synthesis of highly functionalized benzo[ d]thiazol-2(3 H)-ylidene benzamide in the presence of water was accomplished by three-component reaction of ortho-iodoanilines, acrylates, and aroyl isothiocyanates. The protocol involves the in situ generation of thiourea intermediate followed by triethylamine induced intramolecular SNAr displacement reaction and subsequent Michael addition onto acrylate leads to the formation of benzo[ d]thiazol-2(3 H)-ylidene benzamide. Benzo[ b]thiazole is also generated in good yields using amidation and intramolecular aromatic nucleophilic substitution chemistry. The control experiments support the proposed mechanistic pathway. Further X-ray crystallographic studies confirmed the assigned structures of the fused benzamide. |
| Databáze: | OpenAIRE |
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