Reaction of an amide enolate with an alkyl halide

10.1039/sp59 ◽  
2001 ◽  
Author(s):  
Stephen Caddick
Keyword(s):  
2007 ◽  
Vol 360 (8) ◽  
pp. 2661-2668 ◽  
Author(s):  
Badri Z. Momeni ◽  
Saeideh Hamzeh ◽  
Simin S. Hosseini ◽  
Frank Rominger

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.


2017 ◽  
Vol 15 (45) ◽  
pp. 9638-9642 ◽  
Author(s):  
Yaqi Yang ◽  
Zihang Ye ◽  
Xu Zhang ◽  
Yipeng Zhou ◽  
Xiantao Ma ◽  
...  

Alcohols can be efficiently converted into thioethers by a transition metal- and base-free alkyl halide-catalyzed S-alkylation reaction with thiols or disulfides.


1969 ◽  
Vol 47 (17) ◽  
pp. 3271-3273 ◽  
Author(s):  
Harold M. Kolenbrander

A simple method for the synthesis of S-alkyl-DL-homocysteines is described. The method involves the reaction of homocysteine thiolactone with a primary alkyl halide in sodium methoxide solution.


1977 ◽  
Vol 99 (11) ◽  
pp. 3713-3719 ◽  
Author(s):  
Margaret V. Merritt ◽  
Roy A. Johnson

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