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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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01614770
Contributor : Laurent Jonchère <>
Submitted on : Wednesday, October 11, 2017 - 2:00:27 PM
Last modification on : Thursday, July 16, 2020 - 3:17:18 AM

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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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