Cerium (III) chloride as a catalyst in the Clauson-Kaas reaction: Synthesis and reactivity of N-Aryl-2-thiocyanatopyrroles

Current Organic Chemistry

Volumn 16, Issue 12, 2012, Pages 1540-1548

  Silveira, Claudio C ^a   Fortes, Margiani P ^a   Mendes, Samuel R ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b SANTA CATARINA STATE UNIVERSITY   (Brazil)

Author keywords

Cerium chloride; Clauson Kaas synthesis; Microwave assisted reaction; Pyrrol 2 yl disulfides; Pyrrole derivatives; Thiocyanates

Indexed keywords

CATALYSTS; CERIUM COMPOUNDS; MICROWAVE IRRADIATION; SODIUM BOROHYDRIDE; SULFUR COMPOUNDS;

CLAUSA-KAAS SYNTHESIS; CONVENTIONAL HEATING; MICROWAVE- IRRADIATIONS; MICROWAVE-ASSISTED REACTIONS; PHASE TRANSFER; PYRROL-2-YL DISULPHIDE; PYRROLE DERIVATIVES; REACTION SYNTHESIS; THIOCYANATE; ]+ CATALYST;

CHLORINE COMPOUNDS;

EID: 84862608467     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212800672538     Document Type: Article

References (57)

1. Ferreira, V. F.; Souza, M. C. B. V.; Cunha, A. C.; Pereira, L. O. R.; Ferreira, M. L. G. Recent advances in the synthesis of pyrroles. Org. Prep. Proced. Int., 2001, 33, 411-454.
2. Estéves, V.; Villacampa, M.; Menéndez, J. C. Multicomponent reactions for the synthesis of pyrroles. Chem. Soc. Rev., 2010, 39, 4402-4421.
3. Furstner, A. Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years. Angew. Chem. Int. Ed., 2003, 42, 3582-3603.
4. Fan, H.; Peng, J.; Hamman, M. T.; Hu, J.-F. Lamellarins and related pyrrole-derived alkaloids from marine organisms. Chem. Rev., 2008, 108, 264-287.
5. Clauson-Kaas, N.; Tyle, Z. Preparation of cis-and trans-2,5-dimethoxy-2-(acetamidomethyl)-2,5-dihydrofuran, of cis-and trans-2,5-dimethoxy-2-(acetamidomethyl)-tetrahydrofuran, and of 1-phenyl-2-(acetamidomethyl)pyrrole. Acta Chem. Scand., 1952, 6, 667-670.
6. Elming, N.; Clauson-Kaas, N. The preparation of pyrroles from furans. Acta Chem. Scand., 1952, 6, 867-874.
7. Polshetttiwar, V.; Baruwati, B.; Varma, R. S. Magnetic nanoparticlesupported glutathione: a conceptually sustainable organocatalyst. Chem. Commun., 2009, 1837-1839.
8. Polshetttiwar, V.; Varma, R. S. Nano-organocatalyst: magnetically retrievable ferrite-anchored glutathione for microwave-assisted Paal-Knorr reaction, aza-Michael addition, and pyrazole synthesis. Tetrahedron, 2010, 66, 1091-1097.
9. Wilson, M.; Filzen, G.; Welkmaker, G. S. A microwave-assisted, green procedure for the synthesis of N-aryl sulfonyl and N-aryl pyrroles. Tetrahedron Lett., 2009, 50, 4807-4809.
10. Miles, K. C.; Mays, S. M.; Southerland, B. K.; Auvil, T. J.; Ketcha, D. M. The Clauson-Kaas pyrrole synthesis under microwave irradiation. Arkivoc, 2009, xiv, 181-190.
11. Bandyopadhyay, D.; Sanghamitra, M.; Banik, B. K. An expeditious synthesis of N-substituted pyrroles via microwave-induced iodine-catalyzed reactions under solventless conditions. Molecules, 2010, 15, 2520-2525.
12. Azizi, N.; Amiri, A. K.; Ghafuri, H.; Bolourtchian, M.; Saidi, M. R. Ironcatalyzed inexpensive and practical synthesis of N-substituted pyrroles in water. Synlett, 2009, 2245-2248.
13. Abid, M.; Landge, S. M.; Torök, B. An efficient and rapid synthesis of Nsubstituted pyrroles by microwave assisted solid acid catalysis. Org. Prep. Proced. Int., 2006, 38, 495-500.
14. Rivera, S.; Bandyopadhyay, D.; Banik, B. K. Facile synthesis of Nsubstituted pyrroles via microwave-induced bismuth nitrate-catalyzed reaction. Tetrahedron Lett., 2009, 50, 5445-5448.
15. Gourlay, B. S.; Molesworth, P. P.; Ryan, J. H.; Smith, J. A. A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction. Tetrahedron Lett., 2006, 47, 799-801.
16. Zhang, X.; Shi, J. Unique chemoselective Clauson-Kaas reaction of substituted aniline catalyzed by MgI2 etherate. Tetrahedron, 2011, 67, 898-903.
17. Zuo, B.; Chen, J.; Liu, M.; Ding, J.; Wu, H.; Su, W. Scandium triflatecatalysed synthesis of N-substituted pyrroles from amine and 2,5-dimethoxytetrahydrofuran. J. Chem. Res., 2009, 14-16.
18. Toste, F. D.; LaRonde, F.; Still, I. W. J. Thiocyanate as a versatile synthetic unit: efficient conversion of ArSCN to aryl alkyl sulfides and aryl thioesters. Tetrahedron Lett., 1995, 36, 2949-2952.
19. Pilyugin, V. S.; Sapozhnikov, Y. E.; Shitov, G. P. Synthesis of 2-Amino-5(6)-(4-aminophenyl)benzimidazole Derivatives: II. Reaction of 2-nitro-4-thiocyanatoaniline with 4-nitrochlorobenzene. Russ. J. Org. Chem., 2003, 39, 979-984.
20. Tarbell, D. S.; Harnish, D. P. Cleavage of the carbon-sulfur bond in divalent sulfur compounds. Chem. Rev., 1951, 49, 1-90.
21. Riemschneider, R.; Whojan, F.; Orlick, G. Thiocarbamates. III. Aryl thiocarbamates from aryl thiocyanates. J. Am. Chem. Soc., 1951, 73, 5905-5907.
22. Riemschneider, R. Thiocarbamates and related compounds. X. A new reaction of thiocyanates. J. Am. Chem. Soc., 1956, 78, 844-847.
23. Lee, Y. T.; Choi, S. Y.; Chung, Y. K. Microwave-assisted palladiumcatalyzed regioselective cyanothiolation of alkynes with thiocyanates. Tetrahedron Lett., 2007, 48, 5673-5677.
24. Cheeseman, G. W. H.; Hawi, A. A.; Synthesis of some pyrrolobenzothiazepines via N-aryl-2-thiocyanatopyrroles. J. Heterocycl. Chem., 1983, 20, 585-590.
25. Campiani, G.; Nacci, V.; Bechelli, S.; Ciani, S. M.; Garofalo, A.; Fiorini, I, Wikström, H.; Boer, P.; Liao, Y.; Tepper, P. G.; Cagnotto, A.; Mennini, T. New antipsycothic agents with serotonin and dopamine antagonist properties based on a pyrrolo[2,1-b][1,3]benzothiazepine structure. J. Med. Chem., 1998, 41, 3763-3772.
26. Gillis, H. M.; Greene, L.; Thompsom, A. Preparation of sulfenyl pyrroles. Synthesis, 2008, 112-116.
27. Thamyongkit, P.; Bhise, A. D.; Taniguchi, M.; Lindsey, J. S. Alkylthio unit as an i{dotless}-pyrrole protecting group for use in dipyrromethane synthesis. J. Org. Chem., 2006, 71, 903-910.
28. Yadav, J. S.; Reddy, B. V. S.; Krishna, A. D.; Reddy, C. S.; Narsaiah, A. V. Ferric(III) chloride-promoted electrophilic thiocyanation of aromatic and heteroaromatic compounds. Synthesis, 2005, 961-964.
29. Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Iodine/MeOH. A novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics. Tetrahedron Lett., 2004, 45, 2951-2954.
30. Nair, V.; George, T. G.; Nair, L. G.; Panicker, S. B. A direct synthesis of aryl thiocyanates using cerium (IV) ammonium nitrate. Tetrahedron Lett., 1999, 40, 1195-1196.
31. Bhalerao, D. S.; Akamanchi, K. G. Efficient and novel method for thiocyanation of aromatic and heteroaromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate. Synlett, 2007, 2952-2956.
32. Iranpoor, N.; Firouzabadi, F.; Khalili, D.; Shahin, R. A new application for diethyl azodicarboxylate: efficient and regioselective thiocyanation of aromatic amines. Tetrahedron Lett., 2010, 51, 3508-3510.
33. Wu, J.; Wu, G.; Wu, L. Thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and I2O5. Synth. Comm., 2008, 38, 2367-2373.
34. Memarian, H. R.; Baltork, I. M.; Nikoofar, K. Ultrasound-assisted thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and DDQ. Ultrason. Sonochem., 2008, 15, 456-462.
35. Wu, G.; Liu, Q.; Shen, Y.; Wu, W.; Wu, L. Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone. Tetrahedron Lett., 2005, 46, 5831-5834.
36. Bartoli, G.; Marcantoni, E.; Marcolini, M.; Sambri, L. Applications of CeCl3 as an environmental friendly promoter in organic chemistry. Chem. Rev., 2010, 110, 6104-6143.
37. Silveira, C. C.; Mendes, S. R.; Wolf, L.; Martins, G. M. The use of anhydrous CeCl3 as a catalyst for the synthesis of 3-sulfenyl indoles. Tetrahedron Lett., 2010, 51, 2014-2016.
38. Silveira, C. C.; Mendes, S. R.; Líbero, F. M. Solvent-free anti-Markovnikov addition of thiols to alkenes using anhydrous cerium(III) chloride as catalyst. Synlett, 2010, 790-792.
39. Silveira, C. C.; Mendes, S. R.; Líbero, F. M.; Lenardão, E. J.; Perin, G. Glycerin and CeCl3.7H2O: a new and efficient recyclable medium for the synthesis of bis(indolyl)methanes. Tetrahedron Lett., 2009, 50, 6060-6063.
40. Silveira, C. C.; Mendes, S. R.; Rosa, D. D.; Zeni, G. Cerium(III)-mediated efficient and stereoselective hydrochalcogenation of terminal alkynes. Synthesis, 2009, 4015-4021.
41. Silveira, C. C.; Mendes, S. R. Catalytic oxidation of thiols to disulfides using iodine and CeCl3·7H2O in graphite. Tetrahedron Lett., 2007, 48, 7469-7471.
42. Silveira, C. C.; Mendes, S. R.; Wolf, L.; Martins, G. M. Anhydrous CeCl3 catalyzed C3-selective propargylation of indoles with tertiary alcohols. Tetrahedron Lett., 2010, 51, 4560-4562.
43. Ghafuri, H.; Hashemi, M. M. A simple, economical, and catalyst-free oxidation of thiols to disulfides. J. Sulfur Chem., 2009, 30, 578-580.
44. Khan, K. M.; Taha, M.; Ali, M.; Perveen, S. A mild and alternative approach towards symmetrical disulfides using H3IO5/NaHSO3 combination. Lett. Org. Chem., 2009, 6, 319-320.
45. Ding, Y.; Hay, A. S. Cyclic aromatic disulfide oligomers: synthesis and characterization. Macromolecules, 1996, 29, 6386-6392.
46. Priefer, R.; Lee, Y. J.; Barrios, F.; Wosnick, J. H.; Lebuis, A. M.; Farrell, P. G.; Harpp, D. N. Dicubyl disulfide. J. Am. Chem. Soc., 2002, 124, 5626-5627.
47. Guo, H, Zhan, Z.; Zhang, Y. Preparation of dialkyl disulfides via reduction of alkyl thiocyanates with TiCl4/Sm system. Synth. Comm., 1997, 27, 2721-2724.
48. Zhan, Z. P.; Lang, K.; Liu, F.; Hu, L. Water effects on SmI2 reductions. A novel method for the synthesis of alkyl thiols by SmI2-promoted reductions of sodium alkyl thiosulfates and alkyl thiocyanates. Synth. Comm., 2004, 34, 3203-3208.
49. Zong, K.; Chen, W.; Cava, M. P.; Rogers, R. D. Synthesis and properties of bis(2,5-dimethylpyrrolo[3,4-d])tetrathiafulvalenes, a class of annelated tetrathiafulvalene derivatives with excellent electron donor properties. J. Org. Chem., 1996, 61, 8117-8124.
50. Folkins, P. L.; Harpp, D. N. A general methodology for the synthesis of [2.2.1], [3.2.1+], and [4.2.1] bridged bicyclic disulfide systems. J. Org. Chem., 1992, 57, 2013-2017.
51. Burna, C. J.; Field, L. D.; Morgan, J.; Ridley, D.D.; Vignevich, V. Preparation of cyclic disulfides from bisthiocyanates. Tetrahedron Lett., 1999, 40, 6489-6492.
52. Finazzo, C.; Harmer, J.; Bauer, C.; Jaun, B.; Duin, E. C.; Mahlert, F.; Goenrich, M.; Thauer, R. K.; Dooslaer, S. V.; Schweiger, A. Coenzyme B induced coordination of coenzyme M via its thiol group to Ni(I) of F430 in active methyl-coenzyme M reductase. J. Am. Chem. Soc., 2003, 125, 4988-4989.
53. Saint-Jalmes, L. Selective aliphatic fluorination by halogen exchange in mild conditions. J. Fluorine Chem., 2006, 127, 85-90.
54. Makosza, M.; Fedorynski, M. Reactions of organic anions. LII. Reactions of organic thiocyanates with carbanions in aqueous medium. Synthesis, 1974, 274-276.
55. Perrin, D. D.; Armarego, W. L. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1980.
56. Jones, R. A. Pyrrole studies. IX. The infrared spectra of 1-substituted pyrroles. Austr. J. Chem., 1966, 19, 289-296.
57. Wibaut, J. P.; Dhont, J. Thermal rearrangement of some 1-(chlorophenyl)-and 1-(bromophenyl)pyrroles. Rec. Trav. Chim. Pays-Bas, 1943, 62, 272-282.