Silica gel-catalyzed Knoevenagel condensation of peptidyl cyanomethyl ketones with aromatic aldehydes and ketones. A novel Michael acceptor functionality for C-modified peptides: the benzylidene and alkylidene cyanomethyl ketone function

1992 ◽  
Vol 57 (6) ◽  
pp. 1838-1842 ◽  
Author(s):  
Denis Brillon ◽  
Gilles Sauve
2019 ◽  
Vol 18 (1) ◽  
pp. 165-170 ◽  
Author(s):  
Daniel Paprocki ◽  
Stanisław Berłożecki ◽  
Ryszard Ostaszewski

Abstract 3-Cyanopiperidin-2,6-diones are key intermediates in the synthesis of several drugs and natural products. We developed  one-pot synthesis of 3-cyanopiperidin-2,6-diones by Knoevenagel condensation of cyanoacetic acid and aldehydes, followed by addition of cyanoacetic acid, Achmatowicz reaction and decarboxylation. We tested a wide range of aliphatic and aromatic aldehydes. Products were obtained under simple, environmentally friendly conditions and in yields up to 99%. Substrates were stirred in toluene at reflux, and filtered through short pad of silica gel, and the product was purified by recrystallization.


1968 ◽  
Vol 243 (4) ◽  
pp. 848-852
Author(s):  
H W Culp ◽  
R E McMahon

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Vol 91 (5) ◽  
pp. 858-864 ◽  
Author(s):  
Yoshitaka Tsuchido ◽  
Ryota Abe ◽  
Megumi Kamono ◽  
Kimiya Tanaka ◽  
Makoto Tanabe ◽  
...  

ChemInform ◽  
2004 ◽  
Vol 35 (17) ◽  
Author(s):  
Ji-Tai Li ◽  
Yan-Jiang Bian ◽  
Shu-Ming Liu ◽  
Tong-Shuang Li

ChemInform ◽  
2016 ◽  
Vol 47 (6) ◽  
pp. no-no
Author(s):  
Fang-Ming Wang ◽  
Dan Bao ◽  
Bing-Xiang Hu ◽  
Ze-Yu Zhou ◽  
Deng-Deng Huang ◽  
...  

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