A simple protocol for the chemo-selective reduction of imines to the corresponding secondary amines in good yield using inexpensive commercial zinc dust and ammonium formate in methanol at ambient temperature and pressure is described.
HutchinsR.O., and HutchinsM.K., Comprehensive Organic Synthesis, eds FlemingI., and TrostB.M., Pergamon Press, Oxford, 1991, Vol. 8, pp. 60.
2.
DemirA.S., TanyeliC., SesenogluO., and DemicS., Tetrahedron Lett., 1996, 37, 407.
3.
VarmaR.S., and DahiyaR., Tetrahedron, 1998, 54, 6293.
4.
DiabY., LaurentA., and MisonP., Tetrahedron Lett., 1974, 17, 1605.
5.
HaradaK., The chemistry of the carbon–nitrogen double bond, eds PataiS., Interscience Publishers, London, 1970, pp. 255.
6.
HaskelbergL., J. Am. Chem. Soc., 1948, 70, 2811.
7.
AlexanderE.R., and MasegadesA.L., J. Am. Chem. Soc., 1948, 70, 1315.
8.
BottaM., AngelisF.D., GambacortaA., LabbientoL., and NicolettiR., J. Org. Chem., 1985, 50, 1916.
9.
Green, U.S. Pat. No. 3,187,047, 1965; C.A. 53: 9873f.
10.
CipollaL., LayL., NicotraF., PanzaL., and RussoG., J. Chem. Soc. Chem. Commun., 1995, 1993.
11.
Booker-MilburnK.I., DunkinI.R., KellyF.C., KhalafA.I., LearmonthD.A., ProctorG.R., and ScopesD.I.C., J. Chem. Soc. Perkin Trans. 1, 1997, 3261.
12.
PoppF.D., and SchultzH.P., Chem. Rev., 1962, 62, 19.
13.
JohnstoneR.A.W., WilbyA.H., and EntwistleI.D., Chem. Rev., 1985, 85, 129.
14.
ZacharieB., MoreauN., and DockendorffC., J. Org. Chem., 2001, 66, 5264.
15.
ReddyP.G., and BaskaranS., Tetrahedron Lett., 2002, 43, 1919.
16.
SrinivasaG.R., AbirajK., and GowdaD.C., Tetrahedron Lett., 2003, 44, 5835.
17.
BanerjeeA.A., and MukeshD., J. Chem. Soc. Chem. Commun., 1988, 1275.
18.
WieczerzakE., KozlowskaJ., LankiewiczL., and GrzonkaZ., Polish J. Chem., 2002, 76, 1693.
19.
BerdiniV., CestaM.C., CurtiR., AnniballeG., Di BelloN., NanoG., NicliniL., TopaiA., and AllegrettiM., Tetrahedron, 2002, 58, 5669.
20.
BasuB., BhuiyanM.M.H., DasP., and HossainI., Tetrahedron Lett., 2003, 44, 8931.
21.
GowdaD.C., MaheshB., and GowdaS., Indian J. Chem. Sect. B2001, 40B, 75.
22.
GowdaS., AbirajK., and GowdaD.C., Tetrahedron Lett., 2002, 43, 1329.
23.
SrinivasaG.R., NalinaL., AbirajK., and GowdaD.C., J. Chem. Res. (S), 2003, 630.
24.
AbirajK., SrinivasaG.R., and GowdaD.C., Tetrahedron Lett., 2004, 45, 2081.
25.
CorteseN.A., and HeckR.F., J. Org. Chem., 1977, 42, 3491.
26.
EntwistleI.D., JohnstoneR.A.W., and PovallT.J., J. Chem. Soc., Perkin Trans. 1, 1975, 1300.
27.
VogelA.I., Text Book of Practical Organic Chemistry, 5th edn, eds FurnissB.S., HannafordA.J., SmithP.W.G., and TatchellA.R., Addison Wesley Longman Limited, UK, 1997, pp. 1298.
28.
BillmanJ.H., and DiesingA.C., J. Org. Chem., 1957, 22, 1069.
29.
KirsunovA.V., and IvashchenkoY.N., Chem. Abstr., 1953, 30, 1775.
30.
ParkY-T., LeeI. H., and KimY-H.J. Heterocyclic Chem., 1994, 31, 1625.