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Synthesis 2017; 49(19): 4500-4516
DOI: 10.1055/s-0036-1590798
DOI: 10.1055/s-0036-1590798
paper
Synthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation–Iodination and N-Arylation, and Properties Thereof
We thank the Ministère de l’Enseignement supérieur et de la Recherche scientifique Algérien (M.H.), the Centre National de la Recherche Scientifique, the Institut Universitaire de France and Rennes Métropole (F.M.). We acknowledge FEDER founds (D8 VENTURE Bruker AXS diffractometer) and Thermofisher (generous gift of 2,2,6,6-tetramethylpiperidine). This research has been partly performed as part of the CNRS PICS project ‘Bimetallic synergy for the functionalization of heteroaromatics’Weitere Informationen
Publikationsverlauf
Received: 18. Mai 2017
Accepted: 22. Mai 2017
Publikationsdatum:
19. Juli 2017 (online)
Abstract
Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl2·TMEDA (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.
Key words
C–N bond formation - deprotonative metalation - lactam - aromatic compound - antimicrobial activity - antifungal activitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590798.
- Supporting Information
- CIF File
-
References
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