Abstract
The N-monoalkylation of 2- or 3-aminopyridines by a carboxylic acid and sodium borohydride afforded the corresponding alkylaminopyridine under mild conditions in good yields. N-Alkylaminopyridines are important intermediate for preparing N-containing heterocycles, such as “flytrap” aminopyridinium-based anion hosts and pharmaceuticals.
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References
1.
Zakrzewski P.
,
Gowan M.
,
Trimble L.A.
, and
Lau C.K.
, Synthesis , 1999 , 1893 .
2.
Wallace K.J.
,
Belcher W.J.
,
Turner D.R.
,
Syed K.F.
, and
Steed J.W.
, J. Am. Chem. Soc. , 2003 , 125 , 9699 .
3.
Winn M.
,
De B.
,
Zydowsky T.M.
,
Altenbach R.J.
,
Basha F.Z.
,
Boyd S.A.
,
Brune M.E.
,
Buker S.A.
, and
Crowell D.A.
, J. Med. Chem. , 1993 , 36 , 2676 .
4.
Kanie K.
,
Mizuno K.
,
Kuroboshi M.
, and
Hiyama T.
, Bull. Chem. Soc. Jpn. , 1998 , 71 , 1973 .
5.
Traore H.
,
Saunders M.
, and
Michael S.
, Aust. J. Chem. , 2000 , 53 , 951 .
6.
Jacobsen E.J.
,
McCall J.M.
,
Ayer D.E.
,
VanDoornik F.J.
,
Palmer J.R.
,
Belonga K.L.
,
Braughler J.M.
,
Hall E.D.
,
Houser D.J.
,
Krook M.A.
, and
Runge T.A.
, J. Med. Chem. , 1990 , 33 , 1145 .
7.
Balboni G.
,
Marastoni M.
,
Merighi S.
,
Borea P.
, and
Tomatis R.
, Eur. J. Med. Chem. Chim. Ther. , 2000 , 35 , 979 .
8.
Lee J.
,
Shim H.
,
Park Y.
,
Park S.
,
Shin J.
,
Yang W.
,
Lee H.
,
Park W.
,
Chung Y.
, and
Lee S.
, Bioorg. Med. Chem. Lett. , 2002 , 12 , 2715 .
9.
Singh O.M.
,
Singh S.J.
,
Kim S.N.
, and
Lee S.G.
, Bull. korean Chem. Soc. , 2007 , 28 , 115 .
10.
Bernstein J.
,
Stearns B.
,
Dexter L.
, and
Lott W.X.
, J. Am. Chem. Soc. , 1947 , 69 , 1147 .
11.
Fors B.P.
,
Watson D.A.
,
Biscoe M.R.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2008 , 130 , 13552 .
12.
Dubowchik G.M.
,
Michne J.A.
, and
Zuev D.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 3147 .
13.
Bissell E.R.
,
Swansiger R.W.
, J. Chem. Eng. Data , 1981 , 26 , 234 .