A mild and efficient method was developed for the chemo-selective reduction of azo compounds to the corresponding amine/s using recyclable polymer-supported formate as hydrogen donor in the presence of low cost magnesium powder at room temperature.
ParyzekZ., KoenigH., and TabaczkaB., Synthesis, 2003, 2023.
9.
SrinivasaG.R., AbirajK., and GowdaD. C., Tetrahedron Lett., 2003, 44, 5835.
10.
AbirajK., SrinivasaG. R., and GowdaD. C., Synlett, 2004, 877.
11.
(a) HoT.L., and OlahG. A., Synthesis, 1977, 167.
12.
JnaneshwaraG.K., SudalaiA., and DeshpandeV. H., J. Chem. Res., (S), 1998, 160.
13.
GowdaS., AbirajK., and GowdaD. C., Tetrahedron Lett., 2002, 43, 1329.
14.
AbirajK., GowdaS., and GowdaD. C., J. Chem. Res., (S), 2003, 299.
15.
GowdaS., AbirajK., and GowdaD. C., J. Chem. Res., (S), 2002, 384.
16.
SridharaM.B., SrinivasaG. R., and GowdaD. C., Synth Commun., 2004, 34, 1441.
17.
Leading reviews: (a) LeyS.V., BaxendaleI. R., BreamR. N., JacksonP. S., LeachA. G., LongbottomD. A., NesiM., ScottJ. S., StorerR. I., and TaylorS. J., J. Chem. Soc., Perkin Trans., 12000, 3815.
BurtJ., DeanT., and WarrinerS., Chem. Commun., 2004, 454.
23.
MacCossR.N., HenryD. J., BrainC. T., and LeyS. V., Synlett, 2004, 675. (d) M.K.W. Choi and P. H. Toy, Tetrahedron, 2004, 60, 2875, and references therein.
24.
(a) DesaiB., and DanksT. N., Tetrahedron Lett., 2001, 42, 5963.
25.
BasuB., BhuiyanM. M. H., DasP., and HossainI., Tetrahedron Lett., 2003, 44, 8931.
26.
GowdaS., and GowdaD. C., Tetrahedron, 2002, 58, 2211.
The reaction mixture was subjected to shaking using a manual shaker as the shaking of the polymer-supported formate instead of stirring increases its life for recycling purpose.
29.
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.
30.
The Merck Index, eds BudavariS., Merck & Co., Inc., USA, 1989.
