Synthesis of N-Aryl and N-Heteroaryl gamma-, delta-, and epsilon-Lactams Using Deprotometalation-Iodination and N-Arylation, and Properties Thereof - Archive ouverte HAL Access content directly
Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2017

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

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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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Dates and versions

hal-01614770 , version 1 (01-12-2021)

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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: Journal of Synthetic Organic Chemistry, 2017, 49 (19), pp.4500-4516. ⟨10.1055/s-0036-1590798⟩. ⟨hal-01614770⟩
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