The controlled reduction of azoarenes to the corresponding hydrazoarenes using tin and hydrazine hydrate is reported. The reduction proceeds smoothly at room temperature furnishing the hydrazoarene in excellent yield without the formation of an aniline.
RylanderP.N., Hydrogenation Methods, Academic Press, New York, 1985, pp. 168.
3.
(a) JohnstoneR.A.W., WilbyA., and EntwistleI.D., Chem. Rev., 1985, 85, 129; (b) S. Ram and R.E. Ehrenkaufer, Synthesis, 1988, 91; (c) D.C. Gowda and K. Abiraj, Lett. Pept. Sci., 2002, 153.
4.
(a) BanikB.K., BarakatK.J., WagleD.R., ManhasM.S., and BoseA.K., J. Org. Chem., 1999, 64, 5746; (b) D.C. Gowda, Tetrahedron Lett., 2002, 43, 311; (c) A. Wong, J.T. Kuethe and I.W. Davies, J. Org. Chem., 2003, 68, 9865; (d) Z. Paryzek, H. Koenig and B. Tabaczka, Synthesis, 2003, 2023; (e) G.R. Srinivasa, K. Abiraj and D.C. Gowda, Tetrahedron Lett., 2003, 44, 5835; (f) R. Nacario, S. Kotakonda and D.M.D. Fouchard, Org. Lett., 2005, 7, 471.
5.
BertholdH., SchottenT., and HonigH., Synthesis, 2002, 1607.
6.
GowdaS., and GowdaD.C., Tetrahedron, 2002, 58, 2211.
7.
(a) KhanF.A., DashJ., SudheerCh., and GuptaR.K., Tetrahedron Lett., 2003, 44, 7783; (b) S. Gowda, K. Abiraj and D.C. Gowda, Tetrahedron Lett., 2002, 43, 1329.
8.
(a) SrinivasaG.R., AbirajK., and GowdaD.C., Indian J. Chem. Sect. B2003, 42B, 2882; (b) K. Abiraj, G.R. Srinivasa, D.C. Gowda, Aust. J. Chem., 2005, 58, 149.
9.
(a) SelvamP., SonavaneS.U., MohapatraS.K., and JayaramR.V., Tetrahedron Lett., 2004, 45, 3071; (b) S.K. Mohapatra, S.U. Sonavane, R.V. Jayaram and P. Selvam, Org Lett., 2002, 4, 4297.
10.
PereyreM., QuintardJ-P., and RahmA., Tin in Organic Synthesis, Butterworths, Boston, 1987.
11.
(a) LopezR.M., and FuG.C., Tetrahedron, 1997, 53, 16349; (b) P. Shanmugam, R. Srinivasan and K. Rajagopalan, Tetrahedron, 1997, 53, 11685; (c) S. Sano, T. Miwa, X-K. Liu, T. Ishii, T. Takehisa, M. Shiro and Y. Nagao, Tetrahedron: Asymmetry, 1998, 9, 3615.
12.
VogelA.I., Text Book of Practical Organic Chemistry, Addison Wesley Longman Limited, UK, 5th edn, 1997, pp. 1298–1398.
13.
ByronD.J., GuyG.W., and WorrallB.M., J. Chem. Soc., 1965, 3706.
14.
SnyderH.R., WeaverC., and MarshallC.D., J. Am. Chem. Soc., 1949, 71, 289.
