| Autor: |
Hufnagel, Benedikt, Zhu, W. Felix, Franz, Hanna M., Proschak, Ewgenij, Hernández Olmos, Víctor |
| Přispěvatelé: |
Publica |
| Jazyk: |
angličtina |
| Rok vydání: |
2022 |
| Předmět: |
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| Popis: |
A novel oxadiazolone-based method for the synthesis of 3-aminobenzisoxazoles by N-O bond formation and of 2-aminobenzoxazoles through a Tiemann-type rearrangement has been developed. The synthesis of these two pharmaceutically relevant heterocycles was realized by an unexplored retrosynthetic disconnection using a cyclic nitrenoid precursor-based strategy. The selective formation of the two isomers was significantly influenced by steric and electronic effects of substituents. However, tetrabutylammonium chloride (TBACl) efficiently promoted the Tiemann-type rearrangement over N-O bond formation. Control experiments indicate that deprotonation of the phenol induces both rearrangements. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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