Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide

References

• Yin D, He Y, Perera MA, Hong SS, Marhefka C, Stourman N, Kirkovsky L, Miller DD, Dalton JT. Key structural features of nonsteroidal ligands for binding and activation of the androgen receptor. Mol Pharmacol. 2003;63:211–223. doi: 10.1124/mol.63.1.211
   PubMed Web of Science ®Google Scholar
• Guy RG. Chemistry of cyanates and their derivatives. In: Patai S, editor. The chemistry of cyanates and their thio derivatives. New York, NY: John Wiley; 1977.
   Google Scholar
• Loksha Y, El Barbary A, El-Badawi M, Nielsen C, Pedersen E. Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel capravirine analogues. Bioorg Med Chem. 2005;13:4209–4220. doi: 10.1016/j.bmc.2005.04.024
   PubMed Web of Science ®Google Scholar
• Wei ZL, Kozikowski AP. A short and efficient synthesis of the pharmacological research tool GW501516 for the peroxisome proliferator-activated receptor δ. J Org Chem. 2003;68:9116–9118. doi: 10.1021/jo035140g
   PubMed Web of Science ®Google Scholar
• Buchel KH. Chemie der Pflanzen Schutz-Und Schadlingsbe Kampfungsmittle. New York, NY: Springer; 1970. p. 457–459.
   Google Scholar
• Gerson C, Sabater J, Scuri M, Torbati A, Coffey R, Abraham JW, Lauredo I, Forteza R, Wanner A, Salathe M, Abraham WM, Conner GE. The lactoperoxidase system functions in bacterial clearance of airways. Am J Respir Cell Mol Biol. 2000;22:665–671. doi: 10.1165/ajrcmb.22.6.3980
   PubMed Web of Science ®Google Scholar
• Khazaei A, Alizadeh A, Vaghei RG. Preparation of aryl thiocyanates using N, N′-dibromo-N, N′-bis(2, 5-dimethylbenzenesulphonyl) ethylenediamine and N, N-dibromo-2,5-dimethylbenzenesulphonamide in the presence of KSCN as a novel thiocyanating reagent. Molecules. 2001;6:253–257. doi: 10.3390/60300253
   Web of Science ®Google Scholar
• Iranpoor N, Firouzabadi H, Shaterian HR. Efficient one-pot thiocyanation of primary, secondary and tertiary alcohols by in situ generation of Ph3P(SCN)2. A modified procedure. J Chem Res (S). 1999;62:676–677. doi: 10.1039/a906113d
   Google Scholar
• Iranpoor N, Firouzabadi H, Azadi R. A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers. Tetrahedron Lett. 2006;47:5531–5534. doi: 10.1016/j.tetlet.2006.05.145
   Web of Science ®Google Scholar
• Iranpoor N, Firouzabadi H, Nowrouzi N. Preparation of thiocyanates and isothiocyanates from alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/n-Bu4NSCN system. Tetrahedron. 2006;62:5498–5501. doi: 10.1016/j.tet.2006.03.030
   Web of Science ®Google Scholar
• Mokhtari B, Azadi R, Rahmani-Nezhad S. In situ-generated N-thiocyanatosuccinimide (NTS) as a highly efficient reagent for the one-pot thiocyanation or isothiocyanation of alcohols. Tetrahedron Lett. 2009;50:6588–6589. doi: 10.1016/j.tetlet.2009.09.066
   Web of Science ®Google Scholar
• Mokhtari B, Azhdari A, Azadi R. Cyanuric chloride/dimethylformamide promoted one-pot conversion of primary alcohols into alkyl thiocyanates. J Sulfur Chem. 2009;30:585–589. doi: 10.1080/17415990902998603
   Web of Science ®Google Scholar
• Iranpoor N, Firouzabadi H, Bahador H, Jamalian A. Heterogeneous thiocyanation of benzylic alcohols and silyl and THP ethers, and deprotection of silyl and THP-ethers by [PCl3−n(SiO2)n] (Silphos). Phosphorus Sulfur Silicon Relat Elem. 2010;185:1972–1978. doi: 10.1080/10426500903419145
   Web of Science ®Google Scholar
• Khazaei A, Rahmati S, Khalafi-nezhad A, Saednia Sh. Selectfluor™ F-TEDA-BF4 mediated thiocyanation or isothiocyanation of alcohols by in situ generation of [+SCN] under heterogeneous and neutral conditions. J Fluo Chem. 2012;137:123–125. doi: 10.1016/j.jfluchem.2012.03.005
   Web of Science ®Google Scholar
• Mokhtari B, Azadi R, Mardani E. 2-Chloro-1-methylpyridinium iodide, an efficient reagent for the conversion of alcohols into alkyl thiocyanates both under solvent and solvent-free conditions. Tetrahedron Lett. 2012;53:491–493. doi: 10.1016/j.tetlet.2011.11.050
   Web of Science ®Google Scholar
• Hiegel GA, Nguyen J, Zhou, Y. Preparation of alkyl nitrates, nitrites, and thiocyanates from alcohols utilizing trichloroisocyanuric acid with triphenylphosphine. Synth Commun. 2004;34:2507–2511. doi: 10.1081/SCC-200025580
   Web of Science ®Google Scholar
• Sherrington DC, Hodge P. Synthesis and separation using functional polymers. New York, NY: Wiley; 1988.
   Google Scholar
• Ley SV, Baxendale IR, Bream RN, Jackson PS, Leach AG, Longbottom DA, Nesi M, Scott JS, Storer RI, Taylor SJ. Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation. J Chem Soc Perkin Trans. 2000;1:3815–4195. doi: 10.1039/b006588i
   Google Scholar
• Karimi Zarchi MA, Banihashemi R. Green and efficient method for thiocyanation of aromatic and heteroaromatic compounds using cross-linked poly (4-vinylpyridine) supported thiocyanate ion as versatile reagent and oxone as mild oxidant. Phosphorus Sulfur Silicon Relat Elem. 2014;189:1378–1390. doi: 10.1080/10426507.2013.865123
   Web of Science ®Google Scholar
• Karimi Zarchi MA. Polymer-supported thiocyanate as new, versatile and efficient polymeric reagent for conversion of alkyl halides to corresponding alkyl thiocyanates under mild conditions. J Chin Chem Soc. 2007;54:1299–1302.
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Ebrahimi N. An efficient and simple method for diazotization-thiocyanation of aryl amine using cross-linked poly(4-vinylpyridine)-supported thiocyanate ion. Phosphorus Sulfur Silicon Relat Elem. 2012;187:1226–1235. doi: 10.1080/10426507.2012.681407
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Tarabsaz A. Ring opening of epoxides by using cross-linked poly (4- vinylpyridine) supported thiocyanate in the presence of polymer-supported sulfuric acid under solvent-free conditions. Phosphorous Sulfur Silicon Relat Elem. 2014; doi:10.1080/10426507.2014.887079
   Web of Science ®Google Scholar
• Cainelli G, Manescalchi F. Polymer supported reagents. Synthesis of N,N′-dialkylureas, N-alkylurethanes, and thiocyanates from alkyl halides under mild conditions. Synthesis. 1979;141–144. doi: 10.1055/s-1979-28594
   Web of Science ®Google Scholar
• Harrison CR, Hodge P. Polymer-supported reagents: the use of polymer-supported cyanide and thiocyanate to prepare nitriles, thiocyanates, and isothiocyanates. Synthesis. 1980;299–301. doi: 10.1055/s-1980-28999
   Web of Science ®Google Scholar
• Tamami B, Kiasat AR. Synthesis of thiiranes from oxiranes under mild and nonaqueous conditions using polymer supported thiocyanate. Synth Commun. 1996;26:3953–3958. doi: 10.1080/00397919608003817
   Web of Science ®Google Scholar
• Sandler SR. Cyanuric chloride. Novel laboratory hydrochlorinating reagent for alcohols. J Org Chem. 1970;35:3967–3968. doi: 10.1021/jo00836a088
   Web of Science ®Google Scholar
• Gold, H. The reaction of tricyanogen chloride with dimethylformamide. Angew Chem. 1960;72:956–959. doi: 10.1002/ange.19600722406
   Web of Science ®Google Scholar
• Luca LD, Giacomelli G, Porcheddu A. An efficient route to Alkyl chlorides from alcohols using the complex TCT/DMF. Org Lett. 2002;4:553–555. doi: 10.1021/ol017168p
   PubMed Web of Science ®Google Scholar
• Scott MD, Spedding H. Vilsmeier adducts of dimethylformamide. J Chem Soc C. 1986;1603–1609.
   Google Scholar
• Colthup NB, Daly LH, Wiberley SE. Introduction to infrared and Raman spectroscopy. London: Academic Press; 1964.
   Google Scholar
• Karimi Zarchi MA, Tarabsaz A. Versatile and efficient method for synthesis of β-halohydrins via regioselective ring opening reaction of epoxides using cross-linked poly (4-vinylpyridine) supported HCl and HBr under solvent-free conditions. J Polym Res. 2013;20:208–216. doi: 10.1007/s10965-013-0208-3
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Tarabsaz A. A versatile and regioselective synthesis of vicinal Azidoalcohols using cross-linked poly (4-vinylpyridine) supported Azide ion under solvent-free conditions. Chinese J Polym Sci. 2013;31:1660–1669. doi: 10.1007/s10118-013-1362-0
   Web of Science ®Google Scholar
• Turro NJ. Use of electron spins resonance spectroscopy to study the photochemistry of absorbed dibenzyl ketone on porous silica. Tetrahedron. 1987;43:1589–1616. doi: 10.1016/S0040-4020(01)90273-X
   Web of Science ®Google Scholar