Synthesis of N-Aryl and N-Heteroaryl gamma-, delta-, and epsilon-Lactams Using Deprotometalation-Iodination and N-Arylation, and Properties Thereof

Abstract : Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl2TMEDA (M = Zn or Cd; TMEDA =N,N,N,N-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N-arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using dimethyl sulfoxide as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.
Type de document :
Article dans une revue
SYNTHESIS, Georg Thieme Verlag, 2017, 49 (19), pp.4500-4516. 〈10.1055/s-0036-1590798〉
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01614770
Contributeur : Laurent Jonchère <>
Soumis le : mercredi 11 octobre 2017 - 14:00:27
Dernière modification le : vendredi 25 mai 2018 - 01:27:01

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Rim Amara, Ghenia Bentabed-Ababsa, Madani Hedidi, Joseph Khoury, Hacan Awad, et al.. Synthesis of N-Aryl and N-Heteroaryl gamma-, delta-, and epsilon-Lactams Using Deprotometalation-Iodination and N-Arylation, and Properties Thereof. SYNTHESIS, Georg Thieme Verlag, 2017, 49 (19), pp.4500-4516. 〈10.1055/s-0036-1590798〉. 〈hal-01614770〉

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