scholarly journals Synthesis of densely substituted pyridine derivatives from nitriles by a non-classical [4+2] cycloaddition/1,5-hydrogen shift strategy

Author(s):  
Wanqing Wu ◽  
Dandan He ◽  
Kanghui Duan ◽  
Yang Zhou ◽  
Meng Li ◽  
...  

Abstract A novel strategy has been established to assemble an array of densely substituted pyridine derivatives from nitriles and o-substituted aryl alkynes or 1-methyl-1,3-enynes via a non-classical [4 + 2] cycloaddition along with 1,5-hydrogen shift process. The well-balanced affinities of two different alkali metal salts enable the C(sp3)-H bond activation as well as the excellent chemo- and regioselectivities. This protocol offers a new guide to construct pyridine frameworks from nitriles with sp3-carbon pronucleophiles, and shows potential applications in organic synthesis and medicinal chemistry.

2001 ◽  
Vol 12 (10) ◽  
pp. 574-582 ◽  
Author(s):  
Monique Galin ◽  
Andr� Mathis ◽  
Jean-Claude Galin

1978 ◽  
Vol 40 (4) ◽  
pp. 697-698 ◽  
Author(s):  
John P. Kohut ◽  
Kenneth S. Dahl ◽  
Dean C. Luehrs

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