Green synthesis of thiiranes from epoxides catalyzed by magnetically separable CuFe₂O₄/Mg(OH)₂ nanocomposite in water under benign conditions

References

• Dittmer DC. Thiiranes and thiirenes. In: Katritzky AR, Rees CW, editors. Comprehensive heterocyclic chemistry. Vol. 7. Oxford: Pergamon Press; 1984. p. 132–182.
   Google Scholar
• Testero SA, Lee M, Staran RT, et al. Sulfonate-containing thiiranes as selective gelatinase inhibitors. ACS Med Chem Lett. 2011;2:177–181. doi: 10.1021/ml100254e
   Google Scholar
• Hutchinson SA, Baker SP, Linden J, et al. New potent and selective A1 adenosine receptor agonists. Bioorg Med Chem. 2004;12:4877–4884. doi: 10.1016/j.bmc.2004.07.004
   Google Scholar
• Cho H-J, Jung M-J, Kwon Y, et al. Oxiranylmethyloxy or thiiranylmethyloxy-azaxanthones and acridone analogues as potential topoisomerase I inhibitors. Bioorg Med Chem Lett. 2009;19:6766–6769. doi: 10.1016/j.bmcl.2009.09.091
   Google Scholar
• Kellis JT Jr., Childers WE, Robinson CH, et al. Inhibition of aromatase cytochrome P-450 by 10-oxirane and 10-thiirane substituted androgens. Implications for the structure of the active site. J Biol Chem. 1987;262:4421–4426.
   Google Scholar
• Kiasat AR, Kazemi F, Jardi MFM. Solvent-free conversion of oxiranes to thiiranes with thiourea. Phosphorus Sulfur Silicon. 2004;179:1841–1844. doi: 10.1080/10426500490466599
   Google Scholar
• Bouda H, Borredon ME, Delmas M, et al. Reaction in low hydrated solid-liquid heterogeneous medium: thiiranes synthesis from epoxides. Synth Commun. 1987;17:943–951. doi: 10.1080/00397918708063952
   Google Scholar
• Takido T, Kobayashi Y, Itabashi K. A convenient synthesis of thiirans by the use of dimethylthioformamide. Synthesis. 1986;1986:779–780. doi: 10.1055/s-1986-31778
   Google Scholar
• Korn AC, Moroder L. Enantioselective synthesis of diethyl (+)-(2S,3S)-trans-2,3- epithiosuccinate. J Chem Res. 1995;3:102–103.
   Google Scholar
• Brimeyer MO, Mehrota A, Quici S, et al. Silica gel assisted synthesis of thiiranes. J Org Chem. 1980;45:4254–4255. doi: 10.1021/jo01309a047
   Google Scholar
• Zeynizadeh B, Yeghaneh S. A green protocol for solvent-free conversion of epoxides to thiiranes with Dowex-50WX8–supported thiourea. Phosphorus Sulfur Silicon. 2009;184:362–368. doi: 10.1080/10426500802157515
   Google Scholar
• Iranpoor N, Zeynizadeh B. Conversion of epoxides to thiiranes catalyzed with TiO(TFA)2 and TiCl3(Otf) in the presence of ammonium thiocyanate or thiourea. Synth Commun. 1998;28:3913–3918. doi: 10.1080/00397919808004948
   Google Scholar
• Salehi P, Khodaei MM, Zolfigol MA, et al. Magnesium hydrogensulfate: a cheap and efficient catalyst for the conversion of epoxides into β-alkoxy alcohols, vicinal-diols, and thiiranes. Synth Commun. 2003;33:3041–3048. doi: 10.1081/SCC-120022479
   Google Scholar
• Iranpoor N, Kazemi F. Stereospecific formation of S(−) styrene sulfide: efficient conversion of epoxides to thiiranes catalysed with Ru(III). Tetrahedron. 1997;53:11377–11382. doi: 10.1016/S0040-4020(97)00719-9
   Google Scholar
• Yadav JS, Reddy BVS, Baishya G. Indium tribromide: a novel and highly efficient reagent for the conversion of oxiranes to thiiranes. Synlett. 2003;3:396–398. doi: 10.1055/s-2003-37103
   Google Scholar
• Mohammadpoor-Baltork I, Aliyan H. Bismuth (III) chloride; a mild and efficient catalyst for synthesis of thiiranes from oxiranes. Synth Commun. 1998;28:3943–3947. doi: 10.1080/00397919808004952
   Google Scholar
• Bandgar BP, Joshi NS, Kamble VT. 2,4,6-Trichloro-1,3,5-triazine catalyzed synthesis of thiiranes from oxiranes under solvent-free and mild conditions. Tetrahedron Lett. 2006;47:4775–4777. doi: 10.1016/j.tetlet.2006.03.171
   Google Scholar
• Mohammadpoor-Baltork I, Khosropour AR. Bi(TFA)3 and Bi(OTf)3 catalyzed conversions of epoxides to thiiranes with ammonium thiocyanate and thiourea under non-aqueous conditions. Molecules. 2001;6:996–1000. doi: 10.3390/61200996
   Google Scholar
• Yadollahi B, Tangestaninejad S, Habibi MH. Titanium dioxide as a mild and efficient catalyst for conversion of epoxides to thiiranes. Synth Commun. 2004;34:2823–2827. doi: 10.1081/SCC-200026239
   Google Scholar
• Firouzabadi H, Iranpoor N, Khoshnood A. Aluminum tris (dodecyl sulfate) trihydrate Al(DS)3·3H2O as an efficient Lewis acid–surfactant-combined catalyst for organic reactions in water: efficient conversion of epoxides to thiiranes and to amino alcohols at room temperature. J Mol Catal A Chem. 2007;274:109–115. doi: 10.1016/j.molcata.2007.04.035
   Google Scholar
• Moghadam M, Tangestaninejad S, Mirkhani V, et al. Rapid and efficient ring opening of epoxides catalyzed by a new electron deficient tin(IV) porphyrin. Tetrahedron. 2004;60:6105–6111. doi: 10.1016/j.tet.2004.05.069
   Google Scholar
• Moghadam M, Tangestaninejad S, Mirkhani V, et al. High-valent tin(IV) porphyrin, SnIV(TPP)(BF4)2, as an efficient catalyst for the ring opening of epoxides. Catal Commun. 2007;8:2087–2095. doi: 10.1016/j.catcom.2007.04.013
   Google Scholar
• Bandgar BP, Patil AV, Kamble VT, et al. An efficient synthesis of thiiranes from oxiranes using fluoroboric acid adsorbed on silica gel (HBF4-SiO2) as a catalyst under mild conditions in the absence of solvent. J Mol Catal A Chem. 2007;273:114–117. doi: 10.1016/j.molcata.2007.02.051
   Google Scholar
• Mohammadpoor-Baltork I, Khosropour AR. Antimony trichloride; a mild, efficient and convenient catalyst for conversion of oxiranes to thiiranes under non-aqueous conditions. Indian J Chem. 1999;38B:605–606.
   Google Scholar
• Tamami B, Kolahdoozan M. Synthesis of thiiranes from oxiranes in water using polymeric cosolvents. Tetrahedron Lett. 2004;45:1535–1537. doi: 10.1016/j.tetlet.2003.12.014
   Google Scholar
• Wu L, Wang Y, Yan F, et al. Facile conversion of epoxides to thiiranes with ammonium thiocyanate catalyzed with etidronic acid. Bull Korean Chem Soc. 2010;31:1419–1420. doi: 10.5012/bkcs.2010.31.5.1419
   Google Scholar
• Mohammadpoor-Baltork I, Aliyan H. Montmorillonite K-10: a mild, inexpensive and convenient catalyst for synthesis of thiiranes from oxiranes under non-aqueous conditions. J Chem Res. 2000;2000:122–123. doi: 10.3184/030823400103166634
   Google Scholar
• Mirkhani V, Tangestaninejad S, Alipanah L. Mild, efficient, and convenient conversion of oxiranes to thiiranes with ammonium thiocyanate and thiourea in the presence of cerium(IV) polyoxometallate. Synth Commun. 2002;32:621–626. doi: 10.1081/SCC-120002409
   Google Scholar
• Kazemi F, Kiasat AR, Ebrahimi S. LiBF4: a mild and efficient catalyst for conversion of oxiranes to thiiranes with thiourea. Synth Commun. 2003;33:595–600. doi: 10.1081/SCC-120015813
   Google Scholar
• Reddy CS, Nagavani S. Liclo4 catalyzed mild and efficient method for the synthesis of thiiranes from oxiranes. Heteroatom Chem. 2008;19:97–99. doi: 10.1002/hc.20376
   Google Scholar
• Yadav JS, Subba Reddy BV, Sengupta S, et al. Iodine as a mild, efficient, and cost-effective catalyst for the synthesis of thiiranes from oxiranes. Monatsh Chem. 2008;139:1363–1367. doi: 10.1007/s00706-008-0925-1
   Google Scholar
• Kazemi F, Kiasat AR. Facile conversion of epoxides to thiiranes with ammonium thiocyanate catalyzed with oxalic acid. Phosphorus Sulfur Silicon. 2003;178:1333–1337. doi: 10.1080/10426500307898
   Google Scholar
• Iranpoor N, Kazemi F. Cerium(IV) catalysis: efficient conversion of epoxides to thiiranes. Synthesis. 1996;7:821–822. doi: 10.1055/s-1996-4307
   Google Scholar
• Yadav JS, Reddy BVS, Reddy CS, et al. [Bmim]PF6:  A novel and recyclable ionic liquid for conversion of oxiranes to thiiranes in aqueous media. J Org Chem. 2003;68:2525–2527. doi: 10.1021/jo026544w
   Google Scholar
• Surendra K, Krishnaveni NS, Rao KR. A new and efficient method for the synthesis of thiiranes from oxirane–β-cyclodextrin complexes and thiourea in water. Tetrahedron Lett. 2004;45:6523–6526. doi: 10.1016/j.tetlet.2004.06.111
   Google Scholar
• Iranpoor N, Tamami B, Shekarriz M. Conversion of epoxides to thiiranes with thiourea or ammonium thiocyanate catalyzed with poly(4-vinyl pyridine)-Ce(OTf)4. Synth Commun. 1999;29:3313–3321. doi: 10.1080/00397919908085959
   Google Scholar
• Tamami B, Borujeny KP. Synthesis of thiiranes from oxiranes using cross-linked polystyrene supported aluminium chloride as a catalyst. Synth Commun. 2004;34:65–70. doi: 10.1081/SCC-120027239
   Google Scholar
• Liao S, Leutzsch M, Monaco MR, et al. Catalytic enantioselective conversion of epoxides to thiiranes. J Am Chem Soc. 2016;138:5230–5233. doi: 10.1021/jacs.6b01960
   Google Scholar
• Mirza-Aghayan M, Molaee Tavana M. An efficient and improved method for the conversion of oxiranes into thiiranes using graphite oxide. J Sulfur Chem. 2015;36:30–35. doi: 10.1080/17415993.2014.958752
   Google Scholar
• Kaboudin B, Norouzi H. A convenient synthesis of phosphorodithioates and novel conversion of epoxides to thiiranes. Synthesis. 2004;12:2035–2039. doi: 10.1055/s-2004-829176
   Google Scholar
• Zhu Y, Stubbs LP, Ho F, et al. Magnetic nanocomposites: a new perspective in catalysis. Chem Cat Chem. 2010;2:365–374.
   Google Scholar
• Bell AT. The impact of nanoscience on heterogeneous catalysis. Science. 2003;299:1688–1691. doi: 10.1126/science.1083671
   Google Scholar
• Gawande MB, Rathi AK, Branco PS, et al. Sustainable utility of magnetically recyclable nanocatalysts in water: applications in organic synthesis. Appl Sci. 2013;3:656–674. doi: 10.3390/app3040656
   Google Scholar
• Wang T, Zhang L, Wang H, et al. Controllable synthesis of hierarchical porous Fe3O4 particles mediated by poly (diallyldimethylammonium chloride) and their application in arsenic removal. ACS Appl Mater Interfaces. 2013;5:12449–12459. doi: 10.1021/am403533v
   Google Scholar
• Saiz J, Bringas E, Ortiz I. Functionalized magnetic nanoparticles as new adsorption materials for arsenic removal from polluted waters. J Chem Technol Biotechnol. 2014;89:909–918. doi: 10.1002/jctb.4331
   Google Scholar
• Chen B, Zhu Z, Ma J, et al. One-pot, solid-phase synthesis of magnetic multiwalled carbon nanotube/iron oxide composites and their application in arsenic removal. J Colloid Interface Sci. 2014;434:9–17. doi: 10.1016/j.jcis.2014.07.046
   Google Scholar
• Eisavi R, Zeynizadeh B, Baradarani MM. Zeolite molecular sieve 4Å: a reusable catalyst for fast and efficient conversion of epoxides to thiiranes with thiourea. Phosphorus Sulfur Silicon. 2011;186:1902–1909. doi: 10.1080/10426507.2010.550267
   Google Scholar
• Zeynizadeh B, Baradarani MM, Eisavi R. A practical and eco-friendly method for conversion of epoxides to thiiranes with immobilized thiourea on CaCO3. Phosphorus Sulfur Silicon. 2011;186:2208–2215. doi: 10.1080/10426507.2011.583963
   Google Scholar
• Eisavi R, Zeynizadeh B. A green protocol for rapid and efficient conversion of epoxides to thiiranes using alumina immobilized thiourea at solvent-free conditions. Phosphorus Sulfur Silicon. 2016;191:65–69. doi: 10.1080/10426507.2015.1085044
   Google Scholar
• Eisavi R, Ghadernejad S, Zeynizadeh B, et al. Magnetically separable nano CuFe2O4: an efficient and reusable heterogeneous catalyst for the green synthesis of thiiranes from epoxides with thiourea. J Sulfur Chem. 2016;37:537–545. doi: 10.1080/17415993.2016.1196691
   Google Scholar
• Eisavi R, Ahmadi F, Ebadzade B, et al. A green method for solvent-free conversion of epoxides to thiiranes using NH4SCN in the presence of NiFe2O4 and MgFe2O4 magnetic nanocatalysts. J Sulfur Chem. 2017;38:614–624. doi: 10.1080/17415993.2017.1334780
   Google Scholar
• Eisavi R, Alifam S. Znfe2o4 nanoparticles: a green and recyclable magnetic catalyst for fast and regioselective conversion of epoxides to vicinal hydroxythiocyanates using NH4SCN under solvent-free conditions. Phosphorus Sulfur Silicon. 2018;193:211–217. doi: 10.1080/10426507.2017.1390460
   Google Scholar
• Hassanzadeh S, Eisavi R, Abbasian M. Preparation and characterization of magnetically separable MgFe2O4/Mg(OH)2 nanocomposite as an efficient heterogeneous catalyst for regioselective one-pot synthesis of β-chloroacetates from epoxides. Appl Organometal Chem. 2018;32:e4520. doi:10.1002/aoc.4520.
   Google Scholar
• Sun Z, Liu L, Jia DZ, et al. Simple synthesis of CuFe2O4 nanoparticles as gas-sensing materials. Sens Actuators B Chem. 2007;125:144–148. doi: 10.1016/j.snb.2007.01.050
   Google Scholar
• Parvanak Borujeny K. Conversion of oxiranes to thiiranes catalyzed with silica gel-supported aluminium chloride. Synth Commun. 2005;35:2575–2579. doi: 10.1080/00397910500214102
   Google Scholar
• Gorjizadeh M, Afshari M. A facile and convenient method for synthesis of thiiranes under mild condition using phase transfer catalyst. Orient J Chem. 2013;29:1657–1660. doi: 10.13005/ojc/290454
   Google Scholar