Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Iodogen as a Novel Reagent for Diastereoselective Oxidation of Bisnaphthols under Green and Mild Condition

Document Type : Research Article

Authors
Azam Shiri 1
Ahmad Khorramabadi Zad 2
Vahid Bayat 2
1 Department of Applied Chemistry, Faculty of Science, Malayer University, Malayer, I.R. IRAN
2 Faculty of Chemistry, Bu Ali Sina University, Hamedan, I.R. IRAN
Abstract
Iodogen, is a mild and effective reagent that is used mostly for the iodination of biological molecules. However, it is now introduced as a novel reagent for the oxidative cyclization of bisnaphthols to the corresponding Abel’s ketones (spirodienones). Notably, oxidation of bisnaphthols leads to the simultaneous formation of two chiral centers, and hence, two sets of diastereomers. Some oxidizing agents cause the formation of a mixture of these two sets, while others are specific for the distereoselective oxidation of bisnaphthols. Experiments show that only one set of these diastereomeres is selectively formed in high yield with iodogen. An advantage of this diastereoselctive oxidizing agent is that the reaction by-product can be separated and again converted into iodogen through a conventional chlorination reaction by trichloroisocyanuric acid.
Keywords
Iodogen
Diastereoselective
Selective oxidation
Spirodienones
Bisnaphthols
Abel ketones

Subjects

[1] Abel J., Ueber Condensation Zwischen Formaldehyd und Naphtolen, Ber. 25: 3477-3484 (1892).
[2] Kasturi T.R., Pragnacharyulu P.V.P., Reduction of DDHQ and TCC Esters by NaBH4-Its Specificity in the Presence of Alkyl/Aryl Esters, 48(21): 4431-4438 (1992).
[3] Kasturi T.R., Pragnacharyulu P.V.P., Reddy G.M., Jayaram S.K., Singh S.B., Oxidation of Spiroketones with DDQ-Synthesis of Tropone Derivatives and DDHQ Diesters, 48(26): 5481-5496 (1992).
[4] Dean F., Locksley H., Part V. Diastereoisomeric Grisenones Obtained by Oxidative Cyclisation, J. Chem. Soc. 393-401 (1963).
[5] Bennett D., Dean F., Price A., Part VII. Three Isomeric Grisan Derivatives from the Oxidative Cyclisation of Benzylidenebis-2-Naphthol, J. Chem. Soc. 11: 1557-1561 (1970).
[6] Kasturi T.R., Sattigeri J.A., Chemistry of Spirodienones-A brief Overview, Indian Inst. Sci. 74: 487-314 (1994).
[7] Kasturi T.R., Sattigeri J.A., Pragnacharyulu P.V.P., Cameroon T.S., Pradeep B., Reaction of Spironaphthalenones with Hydroxylamine Hydrochloride: Part IV, 51(10): 3051-3060 (1995).
[8] Bennett D.J., Dean F. M., Herbin G.A., Matkin D.A., Price A.W., Robinson M.L., Part 12. Stereochemical Control in the Oxidative Cyclisation of Bisnaphthols, J. Chem. Soc. Perkin Trans. 1: 1978-1985 (1980).
[9] Khoramabadi-Zad A., Yavari I., Shiri A., Bani A., Oxidation of Bisnaphthols to Spironaphthalenones Revisited, Heterocycl. Chem. 45(5): 1351-1358 (2008).
[10] Khorramabadi-Zad A., Shiri A., Derakhshan-Panah F., Salimi Z., Chloramine-T and N-Chlorosuccinimide: Novel Reagents for Diastereoselective Oxidation of Bisnaphthols. Diversity, 14: 829-832 (2010).
[11] Dekhici M., Plihon S., Bar N., Villemin D., Elsiblani H., Cheikh N., Aerobic Copper Catalytic Oxidation of Methylene and Arylidenebisnaphthols: A Green and Efficient Synthesis of Spironaphthalenones, ChemistrySelect, 4: 705-708 (2019).
[12] Khorramabadi-Zad A., Daliran S., Oveisi A.R., Aerial Oxidation of Bisnaphthols to Spironaphthalenones by a Recyclable Magnetic Core-Sell Nanoparticle-Supported TEMPO Catalyst, R. Chimi. 16, 972 (2013).
[13] Alizadeh M., Khodaei M., Moradi K.H., Green and Diasteroselective Oxidative Cyclization of Bisnaphthols to Spirans 7, Iran. Chem. Soc., 7(2): 35-358. (2010).
[14] Khoramabadi-Zad A, Mohammadi S., Azadmanesh M., Diastereoselective Aerial Oxidative Cyclization of Methylenebisnaphthols Catalyzed by N-Hydroxyimides in the Presence of Fe3+ and Co2+-Mn2+ Catalysts, Naturforsch Z., 69: 444-450, (2014).
[15] Oveisi A.R., Khorramabadi-Zad A., Daliran S., Iron-Based Metal–Organic Framework, Fe(BTC): an Effective Dual-Functional Catalyst for Oxidative Cyclization of Bisnaphthols and Tandem Synthesis of Quinazolin-4(3H)-Ones, RSC Adv. 6: 1136-1142 (2016).
[16] Fraker P.J., Speck J.C., Protein and Cell Membrane Iodinations with a Sparingly Soluble Chloroamide, 1,3,4,6-Tetrachloro-3α,6α-Diphenylglycoluril, Biophys. Res. Commun. 80(4): 849-857 (1978).
[17] Ünak T., Akgün Z., Yildirim Y., Duman Y., Erenel G., Self-Radioiodination of Iodogen, Radiat. Isot. 54(5): 749-752 (2001).
[18] Yuan H., Luo J., Field S., Weissleder R., Cantley L., Josephson L., Synthesis and Activity of C11-Modified Wortmannin Probes for PI3 Kinase, Bioconjugate Chem. 16(3): 669-675 (2005).
[19] Safavy A., Georg G.I., Velde D.V., Raisch K.P., Safavy K., Carpenter M., Wang W., Bonner J.A., Khazaeli M.B., Buchsbaum D.J., Site-Specifically Traced Drug Release and Biodistribution of a Paclitaxel-Antibody Conjugate Toward Improvement of the Linker Structure, Bioconjugate Chem. 15: 1264-1268 (2004).
[20] Gupta, Batra S., Jain M., Antibody Labeling with Radioiodine and Radiometals, Methods Mol. Biol. 1141: 147-157 (2014).
[21] Chen J., Wang M., Joyce A., DeFranco D., Kavosi M., Xu X., O'Hara D.M., Comparison of Succinimidyl [(125)I]Iodobenzoate with Iodogen Iodination Methods to Study Pharmacokinetics and ADME of Biotherapeutics. Pharm Res. 31:2810-2821 (2014).
[22] Markwell, M.A.K., Fox, C.F., Surface-Specific Iodination of Membrane Proteins of Viruses and Eucariyotic Cells Using 1,3,4,6-Tetrachloro-3α,6α-Diphenylglycoluril, Biochem. 17(22): 4807-4817 (1978).
[23] Horvath, R.J., Parsons, C.G. Zettler, T.T., Process for Treating Sewage, S. Patent. 3: 445, 383 (1969).
[24] Zettler, T.T., Method of Controlling Algae, S. Patent, 3: 252, 901 (1966).
[25] Shimizu T., Glycoluril as a Slow Release Nitrogen Fertilizer, Soil Sci. Plant Nutr., 33(2): 291-298 (1987).
[26] Khoramabadi-Zad A., Shiri A., Preparation of Several Active N-Chloro-Compounds by Trichloroisocyanuric Acid, 16: 2797-2801 (2009).
[27] Khoramabadi-Zad A., Shiri A., Zolfigol M.A., Mallakpour E., A Novel Reagent for the Oxidation of Urazoles Underheterogeneous Conditions, 16: 2729-2732 (2009).
[28] Fries, H. Güterbock, H. Kühn, Untersuchungen in Der Reihe Des Azimidobenzols und Des N‐Methyl‐Azimidobenzols. Lieb. Ann. Chem. 511: 213-240 (1934).
[29] Ohishi, Kojima T., Matsuoka T., Shiro M., Kotsuki H., High-Yielding TfOH-Catalyzed Condensation of Phenols with Aromatic Aldehydes at High Pressure. A Model Synthesis
of the Benzylidene Biphenol Key Skeleton of Blepharismins. Tet. Lett. 42: 2493-2496 (2001).
[30] Mironov G.S., Vuniil V., Chernakovskaya K.A., Farberov M.I., Einiger Bisphenol, Zh.Org. Khim. 8: 597-600 (1972).
[31] Hewitt J.T., Turner A.J., Ueber die Einwirkung Von β-Naphthol auf Aldehyde, Ber. 34: 202-204 (1901).
[32] Dutta P., Borah R.,Boron Sulfonic Acid (BSA) Catalyzed Selective Synthesis of Aryl-Bis(2-Hydroxynaphth-1-yl)Methanes and 14-Alkyl- and 14-aryl-14H-Dibenzoxanthenes under Solvent-Free Condition, Chem. Lett. 4: 93-100 (2015).
[33] Kolvari E., Koukabi N., Khoramabadi-zadA., Shiri A., Zolfigol M. A., Alternative Methodologies for Halogenation of Organic Compounds, Org. Synth. 4(2): 126-130 (2007).