Pyridinium salts—versatile reagents for the regioselective synthesis of functionalized thiazocino[2,3-b]indoles by tandem dinucleophilic reactions of thiooxindoles

Tetrahedron ◽  
2012 ◽  
Vol 68 (47) ◽  
pp. 9685-9693 ◽  
Author(s):  
Mostafa Kiamehr ◽  
Firouz Matloubi Moghaddam ◽  
Pavel V. Gormay ◽  
Volodymyr Semeniuchenko ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Pyridinium Salts

Mild, General, and Regioselective Synthesis of 2-Aminopyridines from Pyridine N-Oxides via N-(2-Pyridyl)pyridinium Salts

Synlett ◽  
2022 ◽  
Author(s):  
Hui Xiong ◽  
Adam T. Hoye
Keyword(s):  
Reaction Mechanism ◽  
Functional Groups ◽  
Pyridinium Salt ◽  
Regioselective Synthesis ◽  
Pyridinium Salts ◽  
Reaction Sequence ◽  
Sequence Features ◽  
Hydrolytic Decomposition ◽  
Wide Range ◽  
15N Labeling

AbstractA synthesis of 2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt followed by hydrolytic decomposition of the pyridinium moiety to furnish the 2-aminopyridine product. The method is compatible with a wide range of functional groups, is scalable, and features inexpensive reagents. 15N-labeling results gave products consistent with a Zincke reaction mechanism.

ChemInform Abstract: Pyridinium Salts-Versatile Reagents for the Regioselective Synthesis of Functionalized Thiazocino[2,3-b]indoles by Tandem Dinucleophilic Reactions of Thiooxindoles.

ChemInform ◽  
2013 ◽  
Vol 44 (14) ◽  
pp. no-no
Author(s):  
Mostafa Kiamehr ◽  
Firouz Matloubi Moghaddam ◽  
Pavel V. Gormay ◽  
Volodymyr Semeniuchenko ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Pyridinium Salts
Sign in / Sign up

Export Citation Format

Share Document