- Reaction of β-, γ-, and δ-chloroalkanamides with potassium tert-butoxide in tetrahydrofuran: Elimination, and lactamization
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γ- and δ-Chloroalkanamides were found to undergo lactamization readily when treated with potassium tert-butoxide in tetrahydrofuran. Raising the reaction temperature may encourage SN2 displacement reaction. On the other hand β-chloroalkanamides only undergo elimination, followed by dimerization and trimerization of the acrylamide initially formed.
- Wang, Eng Chi,Lin, Huey-Jen
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- Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles
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Transition-metal catalysis has the potential to address shortcomings in the classic SN2 reaction of an amine with an alkyl electrophile, both with respect to reactivity and to enantioselectivity. In this study, we describe the development of a user-friendly method (reaction at room temperature, with commercially available catalyst components) for the enantioconvergent nucleophilic substitution of racemic secondary alkyl halides (α-iodolactams) by indoles. Mechanistic studies are consistent with the formation of a copper(I)-indolyl complex that reacts at different rates with the two enantiomers of the electrophile, which interconvert under the reaction conditions (dynamic kinetic resolution). This investigation complements earlier work on photoinduced enantioconvergent N-alkylation, supporting the premise that this important challenge can be addressed by a range of strategies.
- Bartoszewicz, Agnieszka,Matier, Carson D.,Fu, Gregory C.
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supporting information
p. 14560 - 14564
(2019/10/11)
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- Synthesis of N -Aryl and N -Heteroaryl γ-, δ-, and ?-Lactams Using Deprotometalation-Iodination and N -Arylation, and Properties Thereof
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Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl 2 ·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.
- Amara, Rim,Bentabed-Ababsa, Ghenia,Hedidi, Madani,Khoury, Joseph,Awad, Ha?an,Nassar, Ekhlass,Roisnel, Thierry,Dorcet, Vincent,Chevallier, Floris,Fajloun, Ziad,Mongin, Florence
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p. 4500 - 4516
(2017/09/26)
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- A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles
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(Chemical Equation Presented) Unsaturated keto-lactams undergo sequential conjugate reduction-aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones containing vicinal, fully substituted stereocenters with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization.
- Guazzelli, Giuditta,Duffy, Lorna A.,Procter, David J.
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supporting information; experimental part
p. 4291 - 4294
(2009/06/06)
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