Regioselective and efficient halogenation of 4,5-unsubstituted alkyl 3-hydroxypyrrole/3-hydroxythiophene-2-yl-carboxylates
| Autor: | Laurence Goossens, Paola B. Arimondo, Nathalie Azaroual, Ludovic Halby, Patrick Depreux, Omar Castillo-Aguilera |
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| Přispěvatelé: | Groupe de Recherche sur les formes Injectables et les Technologies Associées - ULR 7365 (GRITA), Université de Lille-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille), Institut de Chimie Pharmaceutique Albert Lespagnol (ICPAL), Université de Lille, Droit et Santé, Centre National de la Recherche Scientifique (CNRS), Maison Française d'Oxford (MFO), Ministère de l'Europe et des Affaires étrangères (MEAE)-Centre National de la Recherche Scientifique (CNRS), Churchill College [Cambridge], University of Cambridge [UK] (CAM) |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
3-Hydroxythiophene
Halogenation [SDV]Life Sciences [q-bio] 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound Drug Discovery Thiophene Organic chemistry [CHIM]Chemical Sciences Reactivity (chemistry) Bromosuccinimide Monobromination Monochlorination Alkyl Pyrrole chemistry.chemical_classification 010405 organic chemistry Organic Chemistry Regioselectivity 0104 chemical sciences chemistry Selectivity 3-Hydroxypyrrole |
| Zdroj: | Tetrahedron Letters Tetrahedron Letters, Elsevier, 2017, 58 (26), pp.2537-2541. ⟨10.1016/j.tetlet.2017.05.025⟩ Tetrahedron Letters, 2017, 58 (26), pp.2537-2541. ⟨10.1016/j.tetlet.2017.05.025⟩ |
| ISSN: | 0040-4039 1873-3581 |
| DOI: | 10.1016/j.tetlet.2017.05.025⟩ |
| Popis: | International audience; Substituted heterocycles, such as pyrrole and thiophene, are commonly found in the field of pharmaceutical and material sciences. Here we studied the reactivity of 4,5-unsubstituted alkyl 3-hydroxypyrrol-2-yl-carboxylates and 4,5-unsubstituted alkyl 3-hydroxythiophen-2-yl-carboxylates in different halogenation conditions, due to their interest as building blocks in the synthesis of bioactive compounds and materials. We describe herein the regioselective monohalogenation of 3-hydroxypyrroles and 3-hydroxythiophenes in mild conditions with common halogenation agents. The selectivity of the halogenation was studied. Optimized one-step reaction conditions were found for monobromination and monochlorination. Finally, we observed that bromination with N-bromosuccinimide (NBS) took place at the C4 position of the heterocycle, while chlorination with SO2Cl2 led to C5-halogenated derivatives. |
| Databáze: | OpenAIRE |
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