A General and Efficient 2-Amination of Pyridines and Quinolines

Jingjun Yin, Bangping Xiang, Mark A. Huffman, Conrad E. Raab, Ian W. Davies

The Journal of Organic Chemistry · 2007 · 178 citations · 25 references

Concepts

Abstract

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.

References

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