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A General and Efficient 2-Amination of Pyridines and Quinolines

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

Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065 jingjun_yin@merck.com; bangping_xiang@merck.com

J. Org. Chem., 2007, 72 (12), pp 4554–4557

DOI: 10.1021/jo070189y

Publication Date (Web): May 15, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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.

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Published In Issue June 08, 2007
Received January 30, 2007

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A General and Efficient 2-Amination of Pyridines and Quinolines