Reduction of aromatic and heteroaromatic azo compounds with hydrazine hydrate

Year 2010, Volume: 14 Issue: 1, 41 - 46, 03.03.2014

Sevim Rollas

Abstract

ABSTRACT: The azo compounds have been reduced with hydrazine hydrate in the presence
of a catalyst or without a catalyst. This reaction is an atractive alternate for the reduction of
azo functional group to obtain new amines. In this review, the reduction of aromatic or heteroaromatic
azo compounds with hydrazine hydrate have been reported.
KEYWORDS: Reduction, azo compounds, uncatalyzed reduction, hydrazine hydrate.

Keywords

Reduction, azo compounds, uncatalyzed reduction, hydrazine hydrate

References

• Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. Vo- gel’s Textbook Practical Organic Chemistry; Wiley: New York, 1989, pp 891.
• Mohapatra SK, Sonavane SU, Jayaram, RV, Selvam, P. Heterogeneous catalytic transfer hydrogenation of aro- matic nitro and carbonyl compounds over cobalt (II) substituted hexagonal mesoporous aluminophosphate moleculer sieves. Tetrahedron Lett, 43: 8527-8529, 2002.
• Khan FA, Dash J, Sudheer CH, Gupta R.K. Chemoselec- tive reduction of aromatic nitro and azo compounds in ionic liquids using zinc and ammonium salts. Tetrahe
• Alonso F, Radivoy G, Yus M. Reduction of hydrazine, azo and azoxy compounds, and amine N-oxides with the Ni-Cl2.2H2O-Li-DTBB (cat.) combination. Tetrahedron, 56: 8673-8678, 2000.
• Mohapatra SK, Sonavane SU, Jayaram RV, Selvam P. Re- ductive cleavage of azo dyes and reduction of nitroarenes over trivalent iron incorporated hexagonal mesoporous aluminophosphate molecular sieves. Applied Catalysis B Environmental, 46: 155-163, 2003.
• Selvam P, Sonavane SU, Mohapatra SK, Jayaram RV. Se- lective reduction of alkenes, α,β-unsaturated carbonyl compounds, nitroarenes, nitroso compounds, N,N-hy- drogenolysis of azo hydrazo functions as well as simulta- neeous hydrodehalogenation and reduction of substituted aryl halides over PdMCM-41 catalyst under transfer hy- drogen conditions. Tetrahedron Lett, 45: 3071-3075, 2004.
• Lauwiner M, Roth R, Rys P. Reduction of aromatic nitro compounds with hydrazine hydrate in the presence of an iron oxide/hydroxide catalyst. III. The selective re- duction of nitro groups in aromatic azo compounds. Ap- plied Catalysis A, 177: 9-14, 1999.
• Kumarraja M, Pitchumani. Simple and efficient reduc- tion of nitroarenes by hydrazine in faujasite zeolites. Ap- plied Cataysis A, 265: 135-139, 2004.
• Staffort WH, Los M, Thomson N. The reduction of azo compounds with hydrazine. Chemistry Industry, 1277, 1956. C.A. 51: 6636a, 1957.
• Gowda DC, Gowda S, Abiraj K. Rapid cleavage azo com- pounds to amine/s using Raney nickel and ammonium formate or formic acid. Indian J Chem Sec B-Org Chem Inc Med Chem, 42: 1774-1776, 2003.
• Phasa MA, Nanjundaswamy HM. Reductive fission of azoarenes to aminoarenes by aluminium/hydrazine hy- drate. J Chem Res, 750-752, 2004.
• Ergenç N, Açıkkol S. Two new azoisoxazole derivatives. J Fac Pharm İstanbul, 8: l0l-108, 1972.
• Ergenç N, Rollas S. p- (Acethylacetonilidenhidyrazono) sulphaguanidine and two new azopyrazoles. J Fac Pharm İstanbul, 10 : 77-86, 1974.
• Ergenç N, Rollas S. Some azopyrazoles I. J Fac Pharm Istanbul, 11: 138-157, 1975.
• Ergenç N, Rollas S. Some azopyrazoles II. J Fac Pharm Istanbul, 11 : 177-182, 1975.
• Rollas, S. Synthesis of 3H-l, 3, 4-Oxadiazoline-2-thione derivatives and Reductive Cleavage with Hydrazine Hydrate. J Fac Pharm İstanbul, 19: 83-88, 1983.
• Ergenç N, Rollas S. Some azopyrazoles IV. J Fac Pharm Istanbul, 13: 139-145, 1977.
• Rollas S, Topaloğlu Y. Synthesis of 2,4-Dihydro-3H-l, 2, 4 triazole-3-thione and 2,3- Dihydro-l,3,4-thiadiazole. J Pharm Univ Mar, 2: 1-6, 1986.
• Özger Y, Rollas S. Reductive cleavage of azo compounds with hydrazine and some 1,3,4-thiadiazole derivatives III. MÜ Fen Bilimleri Dergisi, 5: 133-141, 1988.
• Kocyigit-Kaymakcioglu B, Rollas S, Korcegez E, Ariciog- lu F. Synthesis and biological evaluation of new N-sub- stituted -N’- (3,5-di/1,35,-trimethylpyrazole-4-yl) thiou- rea/urea derivatives Eur J Pharm Sci, 26: 97-103, 2005.
• Rollas S, Ergenç N, Oral B, Koçyiğit-Kaymakçıoğlu B, Özaltın E. A new method for the synthesis of 4-amino- 3,5-dimethylpyrazoles and related compounds. J Fac Pharm Istanbul, 38: 71-78, 2005-2006.
• Ross WCJ, Warwick GP. Reduction of cytotoxic azo com- pounds by hydrazine and by the xanthine oxidase-xan- thine system. Nature, 176: 298-299, 1955.
• Zhang CR, Wang YL. A simple and efficient method for the reduction of azo compounds. Synth Commun, 33: 4205-4208, 2003.
• Pasha MA, Nanjundaswamy HM. Uncatalyzed reduc- tive fission of azoarenes to aminoaren(s) by hydrazine hydrate. Synth Commun, 35: 897-900, 2005.
• Koppes WM, Moran JS, Oxley JC, Smith JL. Azo bond hydrogenation with hydrazine, R-NHNH2, and hydra- zobenzene. Tetrahedron Lett, 49: 3234-3237, 2008.
• Rollas S. Reductive Cleavage of Azo Compounds with Hydrazine Hydrate and some new 1,2,4- triazole deriva- tives II. MÜ Fen Bilimleri Dergisi, 3: 195-200, 1986.
• Rollas S. Reductive Cleavage of Azo Compounds with Hydrazine Hydrate and some new l,3,4-thiadiazole de- rivatives. MÜ Fen Bilimleri Dergisi, 1-2: 59-68, 1985.
• Larsen JW, Freund M, Kim KY, Sidovar M, Stuart JL. Mechanism of the carbon catalyzed reduction of ni- trobenzene by hydrazine. Carbon, 38: 655-661, 2000.
• Gowda S, Abiraj K, Gowda DC. Reductive cleavage of azo compounds catalyzed by commercial zinc dust using ammonium formate or formic acid. Tetrahedron Lett, 43: 1329-1331, 2002.
• Sviridov SI, Vasil’ev, AA, Shorshnev SV. Straightforward transformation of isoxazoles into pyrazoles: renewed and improved. Tetrahedron, 63: 12195-12201, 2007.
• Rollas S. The coupling products by active aliphatic C-H compounds of the diazonium salts and studies on from these certain azopyrazoles. Istanbul University, Pharma- cy Faculty, Doctorate thesis (thesis number: 49), 1974.
• Rollas S. Synthesis and spectrometric analysis of some 1,2,4- triazoline-5- thiones. J Fac Pharm Istanbul, 17: 155- 163, 1981.
• Rollas S. Synthesis and spectroscopic data of some l,3,4- thiadiazoles. J Fac Pharm Istanbul, 18: 3-12, 1982.
• Rollas S. Some l-aroyl-4- alkyl/arylthiosemicarbazides I. Doğa Bilimleri Dergisi: Tıp, 7: 65-73, 1983.
• Dwivedi N, Tewari N, Tiwari VK, Chaturvedi V, Manju YK, Srivastava A, Giakward A, Sinha S, Tripathi RP. An efficient synthesis of aryloxyphenyl cyclopropylmeth- anones: a new class of anti-mycobacterial agents. Bioorg Med Chem Lett, 15: 4526-4530, 2005.
• Vass A, Dudas J, Toth J, Varma RS. Solvent-free reduc- tion of aromatic nitro compounds with alumina-sup- ported hydrazine under microwave irradiation. Tetrahe
• Kumbhar PS, Sanchez-Valente J, Figueras F. Reduction of nitro compounds with hydrazine hydrate in the pres- ence of the iron (III) oxide-MgO catalyst prepared from a Mg-Fe hydrocalcite precursor. Tetrahedron Lett, 39: 2573-2574, 1998.
• Breviglieri G, Giacomo B, Sergio C, Cinzia A, Campanab E, Panunzio M. Reduction of 5-nitrosalicylic acid in wa- ter to give 5-amino-salicylic acid. Molecules, 6: M260, 2001.
• Majid T, Hopkins CR, Pedgrift B, Collar N. Convenient synthesis of 4-amino-3,disubstituted pyrazoles in one- step from the corresponding diketo oximes. Tetrahedron Lett, 45: 2137-2139, 2004.
• Gowda S, Gowda DC. Application of hydrazinium monoformate as new hydrogen donor with raney nickel: a facile reduction of nitro and nitrile moieties. Tetrahe- dron, 58: 2211-2213, 2002.
• Lima LM, Vicente E, Solano B, Perez-Silanes S, Aldana I, Monge A. Unexpected reduction of ethyl 3-phenylqui- onxaline-2-carboxylate 1,4-di-N-oxide derivatives by amines. Molecules, 13: 78-85, 2008.
• Carta A, Paglietti G. A new synthesis of triazolo (4,5-g) quinolines and unexpected ring reduced products by treatment with hydrazine hydrate. Arkivoc, 5: 66-75, 2004.
• Corey EJ, Mock WL, Pasto DJ. Chemistry of diimide. Some new systems for the hydrogenation of multiplet bonds. Tetrahedron Lett, 11: 347-352, 1961.
• Salvador JAR, Leitao AJL, Sa e Melo ML, Hanson JR. Hydrazine hydrate induced reductive cleavage of α,β- epoxy ketones: an efficient procedure for the preparation of β-hydroxy ketones. Tetrahedron Lett, 46: 1067-1070, 2005.