Manganese(III) acetate-mediated oxidative cyclization of α-methylstyrene and trans-stilbene with β-ketosulfones

Molecules

Volumn 18, Issue 4, 2013, Pages 4293-4307

  Bouhlel, Ahlem ^a   Curti, Christophe ^a   Tabelé, Clémence ^a   Vanelle, Patrice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Dihydrofuran; Manganese(III) acetate; Radicals

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENE; ANTIPARASITIC AGENT; CYCLOPROPANE DERIVATIVE; FURAN DERIVATIVE; MANGANESE(III) ACETATE DIHYDRATE; METHYLSTYRENE; ORGANOMETALLIC COMPOUND; STILBENE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS; X RAY;

ACETATES; ALKENES; ANTIPARASITIC AGENTS; CYCLIZATION; CYCLOPROPANES; FURANS; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; STILBENES; STYRENES; X-RAYS;

EID: 84876750847     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18044293     Document Type: Article

References (50)

1. Melikyan, G.G. Manganese(III) mediated reactions of unsaturated systems. Synthesis 1993, 9, 833-850 and references therein.
2. Snider, B.B. Manganese(III)-based oxidative free-radical cyclizations. Chem. Rev. 1996, 96, 339-363 and references therein.
3. Demir, A.S.; Emrullahoglu, M. Manganese(III) acetate: A versatile reagent in organic chemistry. Curr. Org. Synth. 2007, 4, 321-350 and references therein.
4. Burton, J.W. Manganese(III) Acetate, CAN, and Fe(III) Salts in Oxidative Radical Chemistry. In Encyclopedia of Radicals in Chemistry, Biology and Materials, 1st ed.; Chatgilialoglu, C., Studer, A., Eds.; Wiley: Chichester, UK, 2012; Volume 2, pp. 901-943.
5. Keane, H.A.; Hess, W.; Burton, J.W. Manganese(III)-mediated radical cyclizations for the (Z)-selective synthesis of exo-alkylidenepyrrolidinones and pyrrolidines. Chem. Commun. 2012, 48, 6496-6498.
6. Curry, L.; Hallside, M.S.; Powell, L.H.; Sprague, S.J.; Burton, J.W. Manganese(III)-mediated oxidative free-radical cyclisations of allenyl malonates. Tetrahedron 2009, 65, 10882-10892.
7. Davies, J.J.; Krulle, T.M.; Burton, J.W. Total synthesis of 7,11-cyclobotryococca-5,12,26-triene using an oxidative radical cyclization as key step. Org. Lett. 2010, 12, 2738-2741.
8. Citterio, A.; Sebastiano, R.; Marion, A.; Santi, R. Synthesis of substituted tetrahydronaphthalenes by manganese(III), cerium(IV), and iron(III) oxidation of substituted diethyl .alpha.- benzylmalonates in the presence of olefins. J. Org. Chem. 1991, 56, 5328-5335.
9. Bergamini, F.; Citterio, A.; Gatti, N.; Nicolini, M.; Santi, R.; Sebastiano, R. Metal-induced electrochemical oxidation of diethyl benzylmalonates in the presence of alkenes and alkynes. Synthesis of substituted tetrahydro- and dihydro-naphthalenes. J. Chem. Res. 1993, 9, 364-366.
10. Cossy, J.; Leblanc, C. New synthesis of lactams and spirolactams radical cyclization induced by manganese(III) acetate. Tetrahedron Lett. 1989, 30, 4531-4534.
11. Mellor, J.M.; Mohammed, S. Synthesis of oxaspirolactones by manganic acetate promoted addition to exocyclic enol lactones. Tetrahedron 1993, 49, 7547-7556.
12. Bouhlel, A.; Curti, C.; Bertrand, M.P.; Vanelle, P. Access to original spirocyclic derivatives via inter- or intramolecular reaction mediated by manganese(III) acetate. Tetrahedron 2012, 68, 3596-3604.
13. Vanelle, P.; Maldonado, J.; Madadi, N.; Gueiffier, A.; Teulade, J.C.; Chapat, J.P.; Crozet, M.P. SRN1 reactions in imidazo [1, 2-a] pyridine series. Tetrahedron Lett. 1990, 31, 3013-3016.
14. Roubaud, C.; Vanelle, P.; Maldonado, J.; Crozet, M.P. Synthèse et réactions SRN1 en série 3-nitroimidazo[1,2-a]pyrimidine. Tetrahedron 1995, 51, 9643-9656.
15. El-Kashef, H.S.; El-Emary, T.I.; Gasquet, M.; Timon-David, P.; Maldonado, J.; Vanelle, P. New pyrazolo[3,4-b]pyrazines: synthesis and biological activity. Pharmazie 2000, 55, 572-576.
16. Gellis, A.; Kovacic, H.; Boufatah, N.; Vanelle, P. Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents. Eur. J. Med. Chem. 2008, 43, 1858-1864.
17. Cohen, A.; Crozet, M.D.; Rathelot, P.; Vanelle, P. An efficient aqueous microwave-assisted Suzuki-Miyaura cross-coupling reaction in the thiazole series. Green Chem. 2009, 11, 1736-1742.
18. Paloque, L.; Bouhlel, A.; Curti, C.; Dumètre, A.; Verhaeghe, P.; Azas, N.; Vanelle, P. Synthesis and evaluation of monoamidoxime derivatives: Toward new antileishmanial compounds. Eur. J. Med. Chem. 2011, 46, 2984-2991.
19. Bouhlel, A.; Curti, C.; Dumètre, A.; Laget, M.; Crozet, M.D.; Azas, N.; Vanelle, P. Synthesis and evaluation of original amidoximes as antileishmanial agents. Bioorg. Med. Chem. 2010, 18, 7310-7320.
20. Logoglu, E.; Yilmaz, M.; Katircioglu, H.; Yakut, M.; Mercan, S. Synthesis and biological activity studies of furan derivatives. Med. Chem. Res. 2010, 19, 490-497.
21. Findik, E.; Dingil, A.; Karaman, I.; Budak, Y.; Ceylan, M. Synthesis of multi-substituted 4,5-dihydrofuran derivatives from (S)-limonene and 1,3-dicarbonyl compounds and their biological activities. E. J. Chem. 2009, 6, S53-S58.
22. Avetisyan, A.A.; Karapetyan, L.V.; Paronikyan, R.V.; Stepanyan, H.M. Synthesis and antibacterial activity of new 2,5-dihydrofuran derivatives. Pharm. Chem. J. 2011, 45, 156-158.
23. Zhang, Y.; Zhong, H.; Wang, T.; Geng, D.; Zhang, M.; Li, K. Synthesis of novel 2,5-dihydrofuran derivatives and evaluation of their anticancer activity. Eur. J. Med. Chem. 2012, 48, 69-80.
24. Kilroy, T.G.; O'Sullivan, T.P.; Guiry, P.J. Synthesis of dihydrofurans substituted in the 2-position. Eur. J. Org. Chem. 2005, 23, 4929-4949.
25. Cao, W.; Zhang, H.; Chen, J.; Zhou, X.; Shao, M.; McMills, M.C. Stereoselective synthesis of highly substituted trans-2,3-dihydrofuran and trans-2,3-cyclopropane derivatives containing sulfonyl groups. Tetrahedron 2008, 64, 163-167.
26. Lee, J.W.; Dong, Y. I2-Induced Enoletherification of α-Allyl Substituted β-Keto Sulfones; A route to 3-phenylsulfonyl-2,5-disubstituted Furans. Heterocycles 1990, 31, 1417-1421.
27. Feldman, K.S.; Wrobleski, M.L. Alkynyliodonium salts in organic synthesis. Dihydrofuran formation via a formal stevens shift of a carbon substituent within a disubstituted-carbon oxonium ylide. J. Org. Chem. 2000, 65, 8659-8668.
28. Makosza, M.; Judka, M. New reactions of γ-halo carbanions: Simple synthesis of substituted tetrahydrofurans. Chemistry 2002, 8, 4234-4240.
29. Bernard, A.M.; Frongia, A.; Piras, P.P.; Secci, F.; Spiga, M. Regioselective synthesis of trisubstituted 2,3-dihydrofurans from donor-acceptor cyclopropanes or from reaction of the corey ylide with α-sulfenyl-, α-sulfinyl-, or α-sulfonylenones. Org. Lett. 2005, 7, 4565-4568.
30. Curti, C.; Crozet, M.D.; Vanelle, P. Microwave improved manganese(III) acetate based oxidative cyclizations of alkenes with β-ketosulfones. Tetrahedron 2009, 65, 200-205.
31. Qian, C.Y.; Nishino, H.; Kurosawa, K. Manganese(III)-mediated free-radical cyclization of active methylene compounds, alkenes and molecular oxygen. Syntheses of sulfur- and phosphorouscontaining 1,2-dioxa-3-ols. J. Heterocycl. Chem. 1993, 30, 209-216.
32. Shanmugam, P.N.; Hemanth Kumar, K.I.; Perumal, P.N.T. Mn(III) acetate mediated diasteroselective [3+2] oxidative addition of 1,3-dicarbonyl compounds with chalcones. J. Heterocycl. Chem. 2007, 44, 827-830.
33. Sunitha, P.; Shiva Kumar, K.; Rama Rao, B.; Venkateshwarlu, G. Microwave assisted efficient synthesis of β-ketosulfones in aqueous medium. Green Chem. Lett. Rev. 2008, 1, 179-183.
34. Andreani, A.; Leoni, A.; Rambaldi, M.; Locatelli, A.; Bossa, R.; Galatulas, I.; Chiericozzi, M.; Bissoli, M. Dihydropyridines bearing an imidazo[2,1-b]thiazole system. Eur. J. Med. Chem. 1997, 32, 151-157.
35. Suryakiran, N.; Prabhakar, P.; Rajesh, K.; Suresh, V.; Venkatesmarlu, Y. Synthesis of β-ketosulfones using ionic liquid [TPA][Pro] as an efficient and reusable reaction medium. J. Mol. Catal. A Chem. 2007, 270, 20-204.
36. Srinivas, K.; Dubey, P.K. Zinc-mediated tandem-one-pot facile synthesis of 1-(arylsulfonyl)aryl/heteryl methanes: a case of C-S bond formation. Synth. Commun. 2011, 41, 1584-1592.
37. Meek, J.S.; Fowler, J.S. O and S methylation of the ambident p-toluene sulfinate anion. J. Org. Chem. 1968, 33, 3422-3424.
38. Wang, Q.-F.; Hou, H.; Hui, L.; Yan, C.-G. Diastereoselective synthesis of trans-2,3-dihydrofurans with pyridinium ylide assisted tandem reaction. J. Org. Chem. 2009, 74, 7403-7406.
39. Yilmaz, M.; Uzunalioglu, N.; Tarik Pekel, A. Manganese(III) acetate based oxidative cyclizations of 3-oxopropanenitriles with conjugated alkenes and synthesis of 4,5-dihydrofuran-3-carbonitriles containing heterocycles. Tetrahedron 2005, 61, 8860-8867.
40. Deliomeroglu, M.K.; Dengiz, C.; Çalişkan, R.; Balci, M. Mn(OAc)3-promoted sulfur-directed addition of an active methylene compound to alkenes. Tetrahedron 2012, 68, 5838-5844.
41. Garzino, F.; Méou, A.; Brun, P. Asymmetric Mn(III)-based radical synthesis of functionalized 2,3-dihydrofurans. Tetrahedron Lett. 2000, 41, 9803-9807.
42. Ito, Y.; Jogo, S.; Fukuda, N.; Okumura, R.; Nishino, H. Manganese(III) acetate specific intramolecular addition. Synthesis 2011, 9, 1365-1374.
43. Asahi, K.; Nishino, H. Synthesis of bicyclo[3.1.0]hexan-2-ones by manganese(III) oxidation in ethanol. Synthesis 2009, 3, 409-423.
44. Oumar-Mahamat, H.; Moustrou, C.; Surzur, J.-M.; Bertrand, M.P. Lactone synthesis by manganese(III)-mediated oxidative cyclization of allylic beta.-diesters. J. Org. Chem. 1989, 54, 5684-5688.
45. Snider, B.B.; Qinglin, C. Oxidative and dehydrative cyclizations of nitroacetate esters with Mn(OAc)3. Tetrahedron 2002, 58, 7821-7827.
46. Caliskan, R.; Pekel, T.; Watson, W.H.; Balci, M. Unusual oxidative free-radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and oxabenzonorbornadiene. Tetrahedron Lett. 2005, 46, 6227-6230.
47. Borchardt, A.; Kopkowski, A.; Walilewski, W.; Zakrzewski, A. Prace Wydzialu Nauk Technicznych seria A 1990, 18, 35-41.
48. Curti, C.; Laget, M.; Ortiz Carle, A.; Gellis, A.; Vanelle, P. Rapid synthesis of sulfone derivatives as potential anti-infectious agents. Eur. J. Med. Chem. 2007, 42, 880-884.
49. Xiang, J.; Ipek, M.; Suri, V.; Tam, M.; Xing, Y.; Huang, N.; Zhang, Y.; Tobin, J.; Mansour, T.S.; McKew, J. β-Keto sulfones as inhibitors of 11β-hydroxysteroid dehydrogenase type I and the mechanism of action. Bioorg. Med. Chem. 2007, 15, 4396-4405.
50. Enders, D.; Grossmann, A.; Huang, H.; Raabe, G. Dual secondary amine/N-heterocyclic carbene catalysis in the asymmetric Michael/Cross-Benzoin cascade reaction of β-oxo sulfones with enals. Eur. J. Org. Chem. 2011, 23, 4298-4301.