Molecular iodine - An expedient reagent for oxidative aromatization reactions of α,β-unsaturated cyclic compounds

Molecules

Volumn 14, Issue 12, 2009, Pages 5308-5322

  Mphahlele, Malose Jack ^a  

^a UNIVERSITY OF SOUTH AFRICA   (South Africa)

Author keywords

, unsaturated cyclic compounds; Iodine; Oxidative aromatization

Indexed keywords

IODINE;

CATALYSIS; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; REVIEW;

CATALYSIS; CYCLIZATION; IODINE; OXIDATION-REDUCTION;

EID: 73849088721     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14125308     Document Type: Review

References (36)

1. Horning, E.C.; Horning, M.C. Aromatization Studies. IV. Palladium dehydrogenation of arylcyclohexenones to phenols. J. Am. Chem. Soc. 1947, 69, 1359-1361.
2. Horning, E.C.; Horning, M.C; Walker, G.N. Aromatization Studies. VIII. Catalytic dehydrogenation of di- and trialkylcyclohexenones to phenols. J. Am. Chem. Soc. 1949, 71, 169-171.
3. Bondon, D.; Pietrasanta, Y.; Pucci, B. New methods of aromatization of cyclohexenones contained in polycyclic systems. Tetrahedron Lett. 1977, 821-824.
4. Yamaguchi, S.; Yamamoto, K.; Ueda, T.; Morikawa, T.; Kawase, Y. A new preparative method of 4-hydroxybenzofuran-2-carboxylic acid derivatives. Bull. Chem. Soc. Jpn. 1989, 62, 4066-4068.
5. Grieco, P.A.; Marinovic, N. Rhodium-catalyzed migration of double bonds: preparation of substituted phenols and anilines. Tetrahedron Lett. 1978, 29, 2545-2548.
6. Blagbrough, IS.; Pattenden, G.; Raphael, E.F. Isomerization of ω-alkenyl-substituted cyclohexane-1,3-dione enol derivatives using rhodium catalysis. A practical synthesis of substituted resorcinols. Tetrahedron Lett. 1982, 23, 4843-4846.
7. 2-induced oxidative aromatization of a, P-unsaturated cyclohexenones. J. Org. Chem. 1990, 55, 358-360.
8. Moriuch, T.; Kikushima, K.; Kajikawa, T.; Hirao, T. Vanadium-catalyzed oxidative aromatization of 2-cyclohexenones under molecular oxygen. Tetrahedron Lett. 2009, 50, 7385-7387.
9. Kotnis, A.S. A convenient, practical synthesis of substituted resorcinols: Synthesis of DB-2073 and olivetol. Tetrahedron Lett. 1991, 32, 3441-344.
10. Goodwin, S.; Smith, A.F.; Velasquez, A.A.; Horning, E.C. Alkaloids of Lunasia amara. Isolation studies. J. Am. Chem. Soc. 1959, 81, 6209-6213.
11. Mphahlele, M.J.; Hlatshwayo, S.M.; Mogamisi, F.K.; Tsanwani, M.; Mampa, R.M. Iodine-methanol-promoted aromatization of 2-aryl-1,2,3,4-tetrahydro-4- quinolones to 2-aryl-4-methoxyquinolines. J. Chem. Res. (S) 1999, 706-707.
12. Alguinaldo, A.M.; Dalangin-Mallari, V.M.; Macabeo, A.P.G.; Byrne, L.T.; Abe, F.; Yamauchi, T.; Franzblau, S.G. First detection of the plasmid-mediated quinolone resistance determinant qnrA in Enterobacteriaceae clinical isolates in Japan. Int. J. Antimicrobial Agents 2007, 29, 738-739.
13. Singh, O.V.; Kapil S. Oxidation of 2-aryl-1,2,3,4-tetrahydro-4- quinolones: A novel entry for the synthesis of 2- and 3-arylquinoline alkaloids. Synlett 1992, 751-752.
14. Varma, R.S.; Kumar, D. Hypervalent iodine oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones: an expedient route to naturally occurring 4-alkoxy-2-arylquinolines. Tetrahedron Lett. 1998, 39, 9113-9116.
15. Kumar, K.H.; Muralidharan, D.; Perumal, P.T. An efficient oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones employing ferric chloride hexahydrate-methanol: Synthesis of naturally occurring 4-alkoxy-2- arylquinolines. Tetrahedron Lett. 2004, 45, 7903-7906.
16. Banerjee, A.K.; Vera, W.; Mora, H.; Laya, M.S.; Bedoya, L.; Cabrera, E.V. Iodine in organic synthesis. J. Sci. Ind. Res. 2006, 65, 299-308.
17. Togo, H.; Iida, S. Synthetic use of molecular iodine for organic synthesis. Synlett. 2006, 14, 2159-2175.
18. Mphahlele, M.J. Molecular iodine-mediated cyclization of tethered heteroatom-containing alkenyl or alkynyl systems. Molecules 2009, 14, 4814-4837.
19. Stavber, S.; Jereb, M.; Zupan, M. Electrophilic iodination of organic compounds using elemental iodine or iodides. Synthesis 2008, 1487-1513.
20. Tamura, Y.; Yoshimoto, Y. An improved method for the conversion of cyclohexenones into anisoles. Chem. Ind. 1980, 888-889.
21. Kotnis, A.S. A rapid entry to highly functionalized p- methoxybenzoates: Synthesis of the aromatic portion of milbemycin β3. Tetrahedron Lett. 1990, 31, 481-484.
22. Mphahlele, M.J.; Pienaar, A.; Modro, T.A. Reactions of phosphorus-stabilized carbanions with cyclic enones. Aromatization of the substitution and addition products. J. Chem. Soc. Perkin Trans. 2 1996, 1455-1460.
23. Mphahlele, M.J.; Modro, T.A. Reaction of carbanions generated from allylic phosphonates with β-substituted cyclic enones. J. Chem. Soc. Perkin Trans. 1 1996, 2261-2264.
24. Schoop, A.; Greiving, H.; Gohrt, A. A new analogue of rocaglamide by an oxidative dihydrofuran synthesis. Tetrahedron Lett. 2000, 41, 1913-1916.
25. Banerjee, A.K.; Cabrera, E.V.; Azocar, J.A. Iodine-methanol induced novel fragmentation of bicyclic diones to anisole derivatives. Synth. Commun. 2000, 30, 3815-3821.
26. Mphahlele, M.J.; Moekwa, T.B. Iodo- and bromo-enolcyclization of 2-(2-propenyl)cyclohexanediones and 2-(2-propenyl)cyclohexenone derivatives using iodine in methanol and pyridinium hydrobromide perbromide in dichloromethane. Org. Biomol. Chem. 2005, 3, 2469-2475.
27. Kim, J.M.; Lee, K.Y.; Kim, J.N. Oxidative aromatization of 2-acylcyclohexane-1,3-dione derivatives using iodine in methanol. Bull. Korean Chem. Soc. 2003, 24, 1057-1058.
28. Na, J.E.; Kim, J.M.; Lee, S.; Kim, J.N. Synthesis of benzo[b] indeno[2,1-d]furanone skeleton from ninhydrin and cyclohexane-1,3-dione derivatives. Bull. Korean Chem. Soc. 2003, 24, 1725-1726.
29. 2 in MeOH. Bull. Korean Chem. Soc. 2004, 54, 569-572.
30. Kim, J.M.; Lee, K.Y.; Kim, T.H.; Kim, J.N. Synthesis of anisole derivatives from 4-alkylidene-2-cyclohexen-1-ones with iodine in methanol. Bull. Korean Chem. Soc. 2003, 24, 999-1001.
31. Kim, J.M.; Lee, K.Y.; Kim, J.N. Synthesis of 4-methylene-2-cyclohexenones and their aromatization reaction toward para-methoxymethyl anisole derivatives. Bull. Korean Chem. Soc. 2004, 25, 328-330.
32. Horiuchi, C.A.; Fukunishi, H.; Kajita, M.; Yamaguchi, A.; Kiyomiya, H.; Kiji, S. New oxidative aromatization of α,β-unsaturated cyclohexenones with iodine cerium(IV) ammonium nitrate in alcohol. Chem. Lett. 1991, 1921-1924.
33. Lee, Y.R.; Morehead Jr., A.T. A new route for the synthesis of furanoflavone and furanochalcone natural products. Tetrahedron 1995, 51, 4909-4922.
34. Hedge, S.G.; Kassim, A.M.; Ingram, A.I. Aromatization of cyclohexenones with iodine/sodium alkoxide. A regioselective synthesis of 2-iodophenols. Tetrahedron Lett. 1995, 36, 8395-8398.
35. 2-MeOH. Synthesis 2000, 1532-1534.
36. Zeynizadeh, B.; Dilmaghani, K.A.; Roozijoy, A. Aromatization of Hantzsch ester 1,4-dihydropyridines with iodine under normal conditions and ultrasound irradiation. J. Chin. Chem. Soc. 2005, 52, 1001-1004 and references cited therein regarding the use of other oxidizing reagents.