One-Pot Synthesis of Some New α-Bromoketals and Acetals via 1,8-Diazabicyclo[5.4.0] Undec-7-ene-Hydrobromide-Perbromide

Document Type : Research Article

Authors

1 Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, I.R. IRAN

2 Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, P.O. Box 91775-1436 Mashhad, I.R. IRAN

Abstract

α-Bromoketals and acetals are important synthetic precursors in organic synthesis. In this work, some new α-bromoketals are synthesized by the reaction of aryl methyl ketones with diols in the presence of 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) hydrobromide-perbromide in good isolated yields. The latter compound converts aldehydes to acetals and serves as a new and efficient reagent for the synthesis of acetals. Comparative studies of the preparation of  α-bromoketal and acetals using some reported methods versus the present method show that DBUH-Br3 is one of the most efficient reagents for the preparation of these compounds. Conversion of carbonyl compounds to corresponding α-bromoketals and acetals in the presence of DBUH-Br3 under microwave irradiation is also described.

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References

[1] Eaton P.E., The Tricyclo[5.3.0.02,6]Decane System. The Photodimers of Cyclopentenone, J. Am. Chem. Soc., 84: 2344-2348 (1961).
[2] Johnson W.S., Bass J.D., Williamson K.L., Δ2,6-Hexalin-1,5-Dione, Tetrahedron, 19: 861-867 (1963).
[3] Warnhoff E., Marshall D.R., Alpha.-Halo ketones. IV. Reductive Dehalogenation by Substituted Pyridines,J. Org. Chem., 32: 2000-2003 (1963).
[4] Park H.S., Kim S.H., Park M.Y., Kim Y.H., Facile Synthesis of Enol Ethers by Cleavage of α-Bromoacetals and α-Bromoketals Mediated by SmI2, Tetrahedron Lett., 42: 3729-3732 (2001).
[5] Mahdavi H., Haghani E., Malakian B., Cross-Linked Poly(Diallyldimethylammonium Chloride) as an Efficient Solid-Liquid Phase Transfer Catalyst in Reduction of Carbonyl Compounds with Sodium Borohydride, React. Funct. Polym., 66: 1033-1040 (2006).
[6] Mahdavi H., Kachoei, Z., Synthesis and Application of Poly(Diallyldimethylammonium Tribromide) as a Novel Polymeric Brominating Agent, Chin. J. Chem., 28: 2221-2225 (2010).
[7] Karimipour G., Montazerozohori M., Naeini N.H., Manganese (III)-Bis(Salicylaldehyde)-4-Methyl-1,2-Phenylenediimine (Mn-BSMP) as an Inexpensive N2O2 Type Schiff Base Catalyst for Oxidative Decarboxylation of Carboxylic Acids with (n-Bu4NIO4) in the Presence of Imidazol, Iran. J. Chem. Chem. Eng. (IJCCE), 30(4): 13-18 (2011).
[8] Perio B.M., Dozias J., Jacquault P., Hamelin J., Solvent Free Protection of Carbonyl Group under Microwave Irradiation, Tetrahedron Lett., 38: 7867-7870 (1997).
[9] Tateiwa J. Horiuchi H., Uemura S., Ce3+-Exchanged Montmorillonite (Ce3+-Mont) as a Useful Substrate-Selective Acetalization Catalyst, J. Org. Chem., 60: 4039-4043 (1995).
[10] Clerici A., Pastori N., Porta O., Efficient Acetalisation of Aldehydes Catalyzed by Titanium Tetrachloride in a Basic Medium, Tetrahedron, 54: 15679-15690 (1998).
[11] Karimi B., Ashtiani A.M., 2,3-Dichloro-5,6-Dicyano-p-Benzoquinone (DDQ) as a Highly Efficient and Mild Catalyst for Diethyl Acetalization of Carbonyl Compounds, Chem. Lett., 28: 1199-1200 (1999).
[12] Ishihara K., Karumi Y., Kubota M., Yamamoto H., Scandium Trifluoromethanesulfonimide and Scandium Trifluoromethanesulfonate as Extremely Active Acetalization Catalysts, Synlett, 9: 839-841 (1996). 
[13] Bakavoli M., Rahimizadeh M., Eshghi H., Shiri A., Ebrahimpour Z., Takjoo R., Synthesis, Characterization and Structure of DBU-Hydrobromide-Perbromide: A Novel Oxidizing Agent for Selective Oxidation of Alcohols to Carbonyl Compounds, Bull. Korean Chem., 31: 949-952 (2010).
[14] Jafari A., Bakavoli M., Pordel M., 1,8-Diazabicyclo[5.4.0] Undec-7-Ene -Hydrobromide-Perbromide: an Oxidising Agent for One-Pot, J. Chem. Res., 35: 602-604 (2011).
[15] Roman Gh., Vlahakis J.Z., Vukomanovic D., Nakatsu K., Szarek W.A., Heme Oxygenase Inhibition by 1-aryl-2-(1H-imidazol-1-yl/1H-1,2,4-triazol-1-yl)Ethanones and Their Derivatives, Chem. Med. Chem., 5: 1541-1555 (2010).
[16] Rahimizadeh M., Bakavoli M., Shiri A., Eshghi H., Saberi S., 3,3,9,9-Tetramethyl-1,5,7,11-Tetraoxaspiro[5.5]Undecane as a Reagent for Protection of Carbonyl, J. Chem. Res., 2008: 704-706 (2008).
[17] Gregg B.T., Golden K.C., Quinn J.F., Indium(III)Trifluoromethanesulfonate as a Mild, Efficient Catalyst for the Formation of Acetals and Ketals in the Presence of Acid Sensitive Functional Groups, Tetrahedron, 64: 3287-3295 (2008).
[18] Huerta F.F., Gomez C., Yus M., Naphthalene-Catalysed Lithiation of 2-(chlorophenyl)-1,3-Dioxolanes: Generation of Formyl- and Acetyl-Phenyllithium Equivalents, Tetrahedron, 55: 4043-4050 (1999).
[19] Bandgar B.P., Gaikwad N.B.,Solid Supported Reactions and Reagents XIV [1]: Envirocat EPZG® as a Novel Catalyst for Selective Acetalization of Aldehydes and Ketones, Monatsh. Chem., 129: 719-722 (1998).
[20] Cousin D.,Mann J.,NieuwenhuyzenaM., van den Berg H., A New Approach to Combretastatin D2, Org. Biomol. Chem., 4: 54-62 (2006).
[21] Nikishin G.I., Elinson M.N., Makhova I.V., Electrochemical Oxidation of Conjugated Arylolefins to ∝-Bromoketals, Tetrahedron Lett., 29, 1603-1604 (1988).
[22] Svoboda J., Paleček J., Dědek V., Mostecký J., One-Step Synthesis of Substituted 2-Aryl-2-Bromoalkyl-1,3-Dioxolanes, Collect. Czech. Chem. Commun., 49: 1515-1520 (1984).
[23] Cataldo M., Nieddu E., Gavagnin R., Pinna F., Strukul G., Hydroxy Complexes of Palladium(II) and Platinum(II) as Catalysts for the Acetalization of Aldehydes and Ketones, J. Mol. Catal. A: Chemical, 142: 305-316 (1999).
[24] Banik B.K., Chapa M., Marquez J., Cardona M., A Remarkable Iodine-Catalyzed Protection of Carbonyl Compounds, Tetrahedron Lett., 46: 2341-2343 (2005).
[25] Hong M., Xiao G., Bis(perfluorooctanesulfonyl) Imide Supported on Fluorous Silica Gel: Application to Protection of Carbonyls, J. Fluorine Chem., 140: 121-126 (2012).
[26] Mirjalili B.B.F., Zolfigol M.A., Bamoniri A., Hazar A., Acetalization of Carbonyl Compounds by Using Silica-Bound Sulfuric Acid under Green Condition, Bull. Korean Chem. Soc., 25: 865-868 (2004).
[27] Gopinath R., Haque S.J., Patel B.K., Tetrabutylammonium Tribromide (TBATB) as an Efficient Generator of HBr for an Efficient Chemoselective Reagent for Acetalization of Carbonyl Compounds, J. Org. Chem., 67: 5842-5845 (2002).
[28] Shirini F., Imanzadeh G.H., Mousazadeh S.A.R., Mohammadpoor-Baltork I., Abedin M.,A Mild and Efficient Method for the Methoxymethylation and Acetylation of Alcohols Promoted by Benzyltriphenylphosphonium Tribromide, ‎Chin. Chem. Lett., 21: 1187-1190 (2010).
[29] Fahida F., Pourmousavia S.A., Sulfonated Polyanthracene-catalyzed Hghly Efficient and Chemoselective Thioacetalization of Carbonyl Compounds and Transthioacetalization of Acetals and Acylals, J. Sulfur Chem., 36: 16-29 (2015).

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