A General and Efficient 2-Amination of Pyridines and Quinolines

A General and Efficient 2-Amination of Pyridines and Quinolines

Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the...

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Veröffentlicht in:Journal of organic chemistry 2007-06, Vol.72 (12), p.4554-4557
Hauptverfasser: Yin, Jingjun, Xiang, Bangping, Huffman, Mark A, Raab, Conrad E, Davies, Ian W
Format: Artikel
Sprache:eng
Schlagworte:
Amination
Aminopyridines - chemical synthesis
Aminoquinolines - chemical synthesis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Pyridines - chemistry
Quinolines - chemistry
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Beschreibung
Zusammenfassung:Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070189y