Efficient Synthesis and Deprotection of Semicarbazones under Solvent-Free Conditions

Document Type: Research Article

Authors

1 Department of Chemistry, Iran University of Science and Technology, P.O. Box 16846-13114 Tehran, I.R. IRAN

2 Islamic Azad University, East Tehran Branch, Tehran, I.R. IRAN

Abstract

Effective methodologies for efficient preparation of semicarbazones from aldehydes or ketones via milling and the subsequent regeneration of the parent carbonyls by gaseous nitrogen dioxide are described under solid-solid and gas-solid reaction conditions, respectively. These methods are fast, simple and environmentally benign which do not require the use of any auxiliaries such as catalysts or solid supports in their procedures.

Keywords

Main Subjects


[1] Greene T.W., Wust P.G., “Protective Groups in Organic Synthesis”,3rd ed; John Wily & Sons: New York, (1999).
[2] Hanson J.R., “Protective Group in Organic Synthesis”, 1st ed; BlackWell Science, Malden: MA, (1999).
[3] Shriner R.L., Fuson R.C., The Systematic Identification of Organic Compounds, 3rd ed., John Wiley & Sons. Inc., (1980).
[4] Yoa H.C., Resnick P.J.,Azo-Hydrazone Conversion. III. The Autoxidation of Benzaldehyde Phenylhydrazones,J. Org. Chem., 30, p. 2832 (1965).
[5] Fusco R., Sannicolo F., New Rearrangement of Arylhydrazones in Polyphosphoric Acid: Formation of Diaryl Ethers,J. Org. Chem., 46, p. 90 (1981).
[6] Sartori G., Ballini R., Bigi F., Bosica G., Maggi R., Righi P., Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis,Chem. Rev., 104, p. 199 (2004).
[7] Niknam K., Kiasat A.R., Karimi S., Dowex Polymer-Mediated Protection of Carnobyl Groups,Synth. Commun., 35, p. 2231 (2005).
[8] Hajipour A.R., Mohammadpoor-Baltork I., Bigdeli M., A Convenient and Mild Procedure for the Synthesis of Hydrazones and Semicarbazones from Aldehydes or Ketones under Solvent-Free Conditions, J. Chem. Research (S), p. 570 (1999).
[9] Kiasat A.R., Kazemi F., Fallah Mehrjardi M., Synthesis of Semicarbazones from Carbonyl Compounds under Solvent Free Conditions, Asian J. Chem., 17, p. 2830 (2005).
[10] Niknam K., Kiasat A.R., Karami B., Heydari N., Basic Al2O3 as a Recyclable Reagent for the Protection of Carbonyl Groups with Phenylhydrazine Derivatives and Semicarbazides, Turk. J. Chem., 31, p. 135 (2007).
[11] Varma R.S., Dahiya R.,Microwave-Assisted Facile Synthesis of Imines and Enamines Using Envirocat Epzgr as a Catalyst, Synlett., p. 1245 (1997).
[12] Kamakshi R., Boreddy S., Reddy R., Solvent Less Rapid Synthesis of Oxime, Semicarbazone and Phenyl Hydrazone Derivatives from Carbonyl Compound Under Microwave Conditions, Aus. J. Chem., 58, p. 603 (2005).
[13] Bandger B.P., Sadavarte V.S., Uppalla L.S., Govande R., Chemoselective Preparation of Oximes, Semicarbazones, and Tosylhydrazones Without Catalyst and Solvent, Monatsh. Chem., 132, p. 403 (2001).
[14] Kaupp G., Naimi-Jamal M.R., Schmeyers J., Solvent-Free Knoevenagel Condensations and Michael Additions in the Solid State and in the Melt with Quantitative Yield, Tetrahedron, 59,p. 3753 (2003).
[15] Kaupp G., Naimi-Jamal M.R., Stepanenko V., Waste-Free Solid-State Protection of Diols, Diamines, Amino Acids Ond Polyols with Phenylboronic Acid, Chem. Eur. J., 9,p. 4156(2003).
[16] Naimi-Jamal M.R., Mokhtari J., Dekamin M.G., Kaupp G., Sodium Tetraalkoxyborates: Intermediates for the Quantitative Reduction of Aldehydes and Ketones to Alcohols Through Ball Milling with NaBH4, Eur. J. Org. Chem., 21,p. 3567 (2009).
[17] Mokhtari J., Naimi-Jamal M.R., Hamzeali H., Dekamin M.G., Kaupp G., Kneading Ball-Milling and Stoichiometric Melts for the Quantitative Derivatization of Carbonyl Compounds with Gas-Solid Recovery, ChemSusChem., 2,p. 83 (2009).
[18] Mashkouri S., Naimi-Jamal M.R., Mechanochemical Solvent-Free and Catalyst-Free One-Pot Synthesis of Pyrano[2,3-d]Pyrimidine-2,4(1H,3H)-Diones with Quantitative Yields, Molecules, 14, p. 474 (2009).
[19] Kaupp G., Mechanochemistry: the Varied Applications of Mechanical Bond-Breaking, CrystEngComm., 11, p. 388 (2009).
[20] Tullberg E., Schacher F., Peters D., Frejd T.,Solvent-Free Heck-Jeffery Reactions Under Ball-Milling Conditions Applied to the Synthesis of Unnatural Amino Acids Precursors and Indoles, Synthesis,p. 1183 (2006).
[21]  Heravi M.M., Ranjbar L., Derikvand F., Oskooie H.A., Bamoharram F.F., Catalytic Oxidative Cleavage
of C N Bond in the Presence of Mixed-Addenda Vanadomolybdophosphate, H6PMo9V3O40 as a Green and Reusable Catalyst, J. Mol. Catal. A: Chem., 265,p. 186 (2007).
[22] Norouzi M., Tajbakhsh M., Alinezhad H., Geran UrimiG.A., Deprotection of Oximes, Phenylhydrazones, Semicarbazones and Thio-Semicarbazones to the Corresponding Carbonyl Compounds Using Cetyltrimethylammonium Peroxodisulfate as a New and Selective Oxidizing Agent,J. Chin. Chem. Soc., 55, p. 508(2008).
[23] Bandgar B.P., Makone S.S.,Remarkably Fast Deprotection of Semicarbazones and Tosylhydrazones Under Mild, Neutral and Solvent-Free Conditions,J. Chin. Chem. Soc. 47,p. 575 (2000).
[24] Shirini M A., Zolfigol A., Safari I., Mohammadpoor B., Mirjalili B.F.,Regeneration of Carbonyl Compounds by Cleavage of C_N Bonds Under Mild and Completely Heterogeneous Conditions  Tetrahedron Lett., 44,p. 7463 (2003).
[25] Hajipour A.R., Adibi H., Ruoho A.E., Wet Silica-Supported Permanganate for the Cleavage of Semicarbazones and Phenylhydrazones Under Solvent-Free Conditions, J. Org. Chem., 68, p. 4553 (2003).
[26] Heravi M.M., Sabaghian A.J., Bakhtiari Kh., Ghassemzadeh M., Ammonium Chlorochromate adsorbed on Alumina for Clevage of Semicarbones and Phenyldrazones Under Classica Heating and Microwave Irradition in Solvent-Free System, J. Braz. Chem. Soc. 17,p. 614 (2006).
[27] Aghapoor K., Heravi M.M., Nooshabadi M.A., Ghassemzadeh M.,Solid State Cleavage of Semicarbazones with Cerium Ammonium Nitrate Supported by Wet Alumina, Monatsh. Chem., 133, p. 107 (2002).
[28] Mohammadpoor-Baltork I., Sadeghi M.M., Adibi A., Efficient Solvent-Free Oxidation of Organic Compounds with Potassium Dichromate in the Presence of Lewis Acids, Molecules, 6, p. 900 (2001).
[29] Bose D.S., Narraiah A.V., A Facile Method for the Conversion of Oximes andTosylhydrazones to Carbonyl Compounds with Dess-Martin Periodinane,Synth. Commun. 29, p. 937 (1999).
[30] Zhang G.S., Yang D.H., Chen M.F., Cai K., Methylammonium Chlorochromate Adsorbed on Alumina: A Convenient and Efficient Reagent for Cleavage of Carbon-Nitrogen Double Bonds Under Non-Aqueous Condition,Synth. Commun., 28, p. 607 (1998).
[31] Curini M., Rusati O., Pisani E., Costantino U.U., Heterogeneous Catalysis in Carbonyl Regeneration from Oximes, Semicarbazones, and Tosylhydrazones by Zirconium Sulfophenyl Phosphonate, Synlett, p. 333 (1996).
[32] Ram R.N., Varsha K., Regeneration of Carbonyl Compounds from Semicarbazones by Copper (II) Chloride Dihydrate, Tetrahedron Lett., 32,p. 5829 (1991).
[33] Narayanan S., Srinvasan V.S., Stereochemistry of Piperazine-2,5-Dione Formation by Self-Condensation of DL-Amino Acid Esters,J. Chem. Soc. Perkin. Trans., 2, p. 1557 (1986).
[34] Naimi-Jamal M.R., Seyedalikhani M., Mokhtari J., Simple, Efficient and Solvent-Free Method for Quantitative Regeneration of Carbonyl Compounds From Oximes by Gaseous Bromine,Asian J. Chem., 21,p. 3253 (2009).
[35] Mokhtari J., Naimi-Jamal M.R., Hamzeali H., Dekamin M.G., Kaupp G., Kneading Ball-Milling and Stoichiometric Melts for the Quantitative Derivatization of Carbonyl Compounds with Gas-Solid Recovery, ChemSusChem., 2, p. 248, (2009).
[36] Vogel A., “Textbook of Practical Organic Chemistry”, (Eds.: Furniss, B.S ; Hannaford, A. J; Rogers, V; Smith, P. W. G; Tatchell, A. R.), Longman, London, (1986).
[37] Hartough H.D., “Thiophene and Its Derivatives”, Interscience, New York, (1952).
[38] Sabnis R.W., “Handbook of Acid-Base Indicator”, CRC press, New York, (2008).
[39] Hanla M.M., Synthesis and Antibacterial Activity of Some Transition Metal Complexes of Oxime, Semicarbazone and Phenylhydrazone, E-Journal of Chemistry, 6,p. 508 (2009).
[40] Shirini F., Neyestani Z., Abedini, M., KBrO3/MoO3: An Efficient Reagent System for the Oxidative Deprotection of Semicarbazones, 1,1-Diacetates and Acetals, Chinese Chemical Letters, 20, p. 514 (2009).
[41] Shriner, Ralph L., Hermann, Christine K. F., Morrill, Terence C., Curtin, David Y., Fuson, Reynold C., “The Systematic Identification of Organic Compounds”, 8th Edition, John Wiley & Sons, NewYork, (2004).