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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 21
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Original Articles

Efficient Oxidation of Hantzsch 1,4-Dihydropyridines with Tetrabutylammonium Peroxomonosulfate Catalyzed by Manganese(III) Schiff Base Complexes: The Effect of Schiff Base Complex on the Product Selectivity

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Pages 3867-3879 | Received 23 Jan 2009, Published online: 07 Oct 2009

REFERENCES

  • (a) Zamponi , G. W. ; Stotz , S. C. ; Staples , R. J. ; Andro , T. M. ; Nelson , J. K. ; Hulubei , V. ; Blumenfeld , A. ; Natale , N. R. Unique structure–activity relationship for 4-isoxazolyl-1,4-dihydropyridines . J. Med. Chem. 2003 , 46 , 87 – 96 ; (b) Zarghi , A. ; Sadeghi , H. ; Fassihi , A. ; Faizi , M. ; Shafiee , A. Synthesis and calcium antagonist activity of 1,4-dihydropyridines containing phenylaminoimidazolyl substituents . Farmaco 2003 , 58 , 1077 – 1081 ; (c) Peri , R. ; Padmanabhan , S. ; Rutledge , A. ; Singh , S. ; Triggle , D. J. Permanently charged chiral 1,4-dihydropyridines: Molecular probes of L-type calcium channels: Synthesis and pharmacological characterization of methyl (ω-trimethylalkylammonium) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate iodide, calcium channel antagonists . J. Med. Chem. 2000 , 43 , 2906 – 2914 .
  • (a) Poindexter , G. S. ; Bruce , M. A. ; Breitenbucher , J. G. ; Higgins , M. A. ; Sit , S. Y. ; Romine , J. L. ; Martin , S. W. ; Ward , S. A. ; McGovern , R. T. ; Clarke , W. ; Russell , J. ; Antal-Zimanyi , I. Dihydropyridine neuropeptide Y Y1 receptor antagonists 2: Bioisosteric urea replacements . Bioorg. Med. Chem. 2004 , 12 , 507 – 521 ; (b) Poindexter , G. S. ; Bruce , M. A. ; LeBoulluec , K. L. ; Monkovic , I. ; Martin , S. W. ; Parker , E. M. ; Ben , L. G. ; McGovern , R. T. ; Ortiz , A. A. ; Stanley , J. A. ; Mattson , G. K. ; Kozlowski , M. ; Arcuri , M. ; Antal-Zimanyi , I. Dihydropyridine neuropeptide Y Y1 receptor antagonists . Bioorg. Med. Chem. Lett. 2002 , 12 , 379 – 382 .
  • Eharkar , P. S. ; Desai , B. ; Gaveria , H. ; Varu , B. ; Loriya , R. ; Naliapara , Y. ; Shah , A. ; Kulkarni , V. M. Three-dimensional quantitative structure–activity relationship of 1,4-dihydropyridines as antitubercular agents. J. Med. Chem. 2002, 45, 4858–4867.
  • (a) McCormack , J. G. ; Westergaard , N. ; Kristiansen , M. ; Brand , C. L. ; Lau , J. Pharmacological approaches to inhibit endogenous glucose production as a means of anti-diabetic therapy . Curr. Pharm. Des. 2001 , 7 , 1451 – 1474 ; (b) Ogawa , A. K. ; Willoughby , C. A. ; Raynald , B. ; Ellsworth , K. P. ; Geissler , W. M. ; Myer , R. W. ; Yao , J. ; Georgianna , H. ; Chapman , K. T. Glucose-lowering in a db/db mouse model by dihydropyridine diacid glycogen phosphorylase inhibitors . Bioorg. Med. Chem. Lett. 2003 , 13 , 3405 – 3408 .
  • (a) Boer , R. ; Gekeler , V. Chemosensitizers in tumor therapy: New compounds promise better efficacy . Drugs Fut. 1995 , 20 , 499 – 509 ; (b) Sabitha , G. ; Kiran Kumar Reddy , G. S. ; Srinivas Reddy , C. ; Yadav , J. S. A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature . Tetrahedron Lett. 2003 , 44 , 4129 – 4131 .
  • (a) Katsuki , T. Mn–salen catalyst, competitor of enzymes, for asymmetric epoxidation . J. Mol. Catal. A: Chem. 1996 , 113 , 87 – 107 ; (b) Katsuki , T. Catalytic asymmetric oxidations using optically active (salen) manganese(III) complexes as catalysts . Coord. Chem. Rev. 1995 , 140 , 189 – 214 .
  • Ortiz de Montellano , P. R. Cytochrome P-450: Structure, Mechanism, and Biochemistry, , 2nd ed. ; Plenum Press : New York , 1995 .
  • (a) Routier , S. B. ; Bernier , J. L. ; Catteau , M. P. ; Bailly , C. Highly preferential cleavage of unpaired guanines in DNA by a functionalized salen–nickel complex . Bioorg. Med. Chem. Lett. 1997 , 7 , 63 – 66 ; (b) Muller , J. G. ; Paikoff , S. J. ; Rokita , S. E. ; Burrow , C. J. DNA modification promoted by water-soluble nickel(II) salen complexes: A switch to DNA alkylation . J. Inorg. Biochem. 1994 , 54 , 199 – 206 ; (c) Samide , M. J. ; Peters , D. G. Electrochemical reduction of copper(II) salen at carbon cathodes in dimethylformamide . J. Electroanal. Chem. 1998 , 443 , 95 – 102 ; (d) Mirkhani , V. ; Tangestaninejad , S. ; Moghadam , M. ; Moghbel , M. Rapid and efficient oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by manganese(III) Schiff base complexes . Bioorg. Med. Chem. 2004 , 12 , 903 – 906 ; (e) Puglisi , A. ; Tabbi , G. ; Vecchio , G. Bioconjugates of cyclodextrins of manganese salen-type ligand with superoxide dismutase activity . J. Inorg. Biochem. 2004 , 98 , 969 – 976 .
  • (a) Palucki , M. ; McCormick , G. J. ; Jacobsen , E. N. Low temperature asymmetric epoxidation of unfunctionalized olefins catalyzed by (salen)Mn(III) complexes . Tetrahedron Lett. 1995 , 36 , 5457 – 5460 ; (b) Adam , W. ; Jeco , J. ; Levai , A. ; Nemes , C. ; Patonay , T. ; Sebok , P. Enantioselective epoxidation of 2,2-dimethyl-2H-chromenes by dimethyldioxirane and Jacobsen's Mn(III) salen catalysts . Tetrahedron Lett. 1995 , 36 , 3669 – 3672 ; (c) Linker , T. The Jacobsen-Katsuki epoxidation and its controversial mechanism . Angew. Chem., Int. Ed. Engl. 1997 , 36 , 2060 – 2062 ; (d) Irie , R. ; Hashihayata , T. ; Katasuki , T. ; Akita , M. ; Moro-oka , M. X-ray structures of chiral (salen)manganese(III) complexes: Proof of pliability of the salen ligand . Chem. Lett. 1998 , 1041 – 1042 ; (e) Hamada , T. ; Fukuda , H. ; Katsuki , T. Mechanism of one oxygen atom transfer from oxo (salen)manganese(V) complex to olefins . Tetrahedron 1996 , 52 , 515 – 530 .
  • (a) Adam , W. ; Roschmann , K. J. ; Saha-Moller , C. R. ; Seebach , D. cis-Stilbene and (1α,2β,3α)-(2-ethenyl-3-methoxycyclopropyl)benzene as mechanistic probes in the Mn(III)(salen)-catalyzed epoxidation: Influence of the oxygen source and the counterion on the diastereoselectivity of the competitive concerted and radical-type oxygen transfer. J. Am. Chem. Soc. 2002, 124, 5068–5073; (b) Campbell , K. M. ; Lashley , M. R. ; Wayatt , J. K. ; Nantz , M. H. ; Britt , R. D. Dual-mode EPR study of Mn(III) salen and the Mn(III) salen-catalyzed epoxidation of cis-β-methylstyrene. J. Am. Chem. Soc. 2001, 123, 5710–5719.
  • (a) Öhberg , L. ; Westman , J. An efficient and fast procedure for the Hantzsch dihydropyridine synthesis under microwave conditions . Synlett 2001 , 1296 – 1298 ; (b) Zolfigol , M. A. ; Safaiee , M. Synthesis of 1,4-dihydropyridines under solvent-free conditions . Synlett 2004 , 827 – 828 .
  • Vanden Eynde , J. J. ; Mayence , A. ; Maquestiau , A. A novel application of the oxidizing properties of pyridinium chlorochromate: Aromatization of Hantzsch 1,4-dihydropyridines . Tetrahedron 1992 , 48 , 463 – 468 .
  • Sabitha , G. ; Kumar Reddy , G. S. K. ; Reddy , C. S. ; Fatima , N. ; Yadav , J. S. Zr(NO3)4: A versatile oxidizing agent for aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines . Synthesis 2003 , 1267 – 1271 .
  • Pfister , J. R. Rapid, high-yield oxidation of Hantzsch-type 1,4-dihydropyridines with ceric ammonium nitrate . Synthesis 1990 , 689 – 690 .
  • Anniyappan , M. ; Muralidharan , D. ; Paramasivan , P. T. A novel application of the oxidizing properties of urea nitrate and peroxydisulfate–cobalt(II): Aromatization of NAD(P)H model Hantzsch 1,4-dihydropyridines . Tetrahedron 2002 , 58 , 5069 – 5073 .
  • Nakamichi , N. ; Kawashita , Y. ; Hayashi , M. Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid . Org. Lett. 2002 , 4 , 3955 – 3957 .
  • (a) Memarian , H. R. ; Sadeghi , M. M. ; Aliyan , H. Photochemistry of some 1,4-dihydropyridine derivatives: Part I . Indian J. Chem. 1998 , 37B , 219 – 223 ; (b) Memarian , H. R. ; Abdoli-Senejani , M. ; Tangestaninejad , S. Photosensitized oxidation of unsymmetrical 1,4-dihydropyridines . J. Iran. Chem. Soc. 2006 , 3 , 285 – 292 ; (c) Zhang , D. ; Wu , L. Z. ; Zhou , L. ; Han , X. ; Yang , Q. Z. ; Zhang , L. P. ; Tung , C. J. Photocatalytic hydrogen production from Hantzsch 1,4-dihydropyridines by platinum(II) terpyridyl complexes in homogeneous solution . J. Am. Chem. Soc. 2004 , 126 , 3440 – 3441 .
  • (a) Nasr-Esfahani , M. ; Moghadam , M. ; Tangestaninejad , S. ; Mirkhani , V. Biomimetic oxidation of Hantzsch 1,4-dihydropyridines with tetra-n-butylammonium periodate catalyzed by tetraphenyl porphyrinatomanganese(III) chloride [Mn(TPP)Cl]. Bioorg. Med. Chem. Lett. 2005, 15, 3276–3278; (b) Nasr-Esfahani , M. ; Moghadam , M. ; Tangestaninejad , S. ; Mirkhani , V. ; Momeni , A. R. Rapid and efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by manganese(III) Schiff base complexes. Bioorg. Med. Chem. 2006, 14, 2720–2724; (c) Moghadam , M. ; Nasr-Esfahani , M. ; Tangestaninejad , S. ; Mirkhani , V. ; Zolfigol , M. A. Biomimetic aromatization of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by a new polystyrene-bound manganese porphyrin. Can. J. Chem. 2006, 84, 1–4; (d) Moghadam , M. ; Nasr-Esfahani , M. ; Tangestaninejad , S. ; Mirkhani , V. Mild and efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by a new polystyrene-bound Mn(TPP)Cl. Bioorg. Med. Chem. Lett. 2006, 16, 2026–2030; (e) Montazerozohori , M. ; Karami , B. ; Nasr-Esfahani , M. ; Musavi , S. A. Silver salts/iodine monochloride as a new oxidation system for the oxidative aromatization of 1,4-dihydropyridines. Heterocycl. Commun. 2007, 13, 289–295.
  • (a) Zolfigol , M. A. ; Kiany-Borazjani , M. ; Sadeghi , M. M. ; Mohammadpoor-Baltork , I. ; Memarian , H. R. An efficient method for the oxidation of Hantzsch 1,4-dihydropyridines to their corresponding pyridine derivatives under mild and heterogeneous conditions . Synth. Commun. 2000 , 30 , 551 – 558 ; (d) Zolfigol , M. A. ; Kiany-Borazjani , M. ; Sadeghi , M. M. ; Mohammadpoor-Baltork , I. ; Memarian , H. R. Aromatization of 1,4-dihydropyridines under mild and heterogeneous conditions . Synth. Commun. 2000 , 30 , 3919 – 3923 ; (e) Zolfigol , M. A. ; Bagherzadeh , M. ; Niknam , K. ; Shirini , F. ; Mohammadpoor-Baltork , I. ; Ghorbani Choghamarani , A. ; Baghbanzadeh , M. Oxidation of 1,4-dihydropyridines under mild and heterogeneous conditions using solid acids . J. Iran. Chem. Soc. 2006 , 3 , 73 – 80 .
  • Nakamichi , N. ; Kawashita , Y. ; Hayashi , M. Activated carbon-promoted oxidative aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines using molecular oxygen . Synthesis 2004 , 1015 – 1020 .
  • (a) Delgado , F. ; Alvarez , C. ; Garcia , O. ; Penieres , G. ; Marquez , C. Unusual oxidative dealkylation of certain 4-alkyl-1,4-dihydropyridines with MnO2/bentonite using microwave irradiation, in the absence of solvent (II) . Synth. Commun. 1991 , 21 , 2137 – 2141 ; (b) Böker , R. H. ; Guengerich , F. P. Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450 . J. Med. Chem. 1986 , 29 , 1596 – 1603 .
  • Starks , C. ; Liotta , C. ; Halpern , M. Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspective ; Chapman & Hall : New York , 1994 .
  • Trost , B. M. ; Braslau , R. Tetra-n-butylammonium oxone: Oxidations under anhydrous conditions . J. Org. Chem. 1988 , 53 , 532 – 537 .
  • Meunier , B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage . Chem. Rev. 1992 , 92 , 1411 – 1456 .
  • Strukul , G. ; Sinigalia , R. ; Zanardo , A. ; Pinna , F. ; Michelin , R. A. Selective oxidations of olefins catalyzed by platinum(II) complexes: Use of tert-butyl hydroperoxide and potassium caroate as oxidants: Ketone vs. epoxide formation . Inorg. Chem. 1989 , 28 , 554 – 559 .
  • Wessel , J. ; Crabtree , R. H. Nonradical tetrabutylammonium monopersulfate oxidation of hydrocarbons catalyzed by [Mn3O4bipy4(H2O)2](ClO4)4 . J. Mol. Cat. A: Chem. 1996 , 113 , 13 – 22 .
  • Mohajer , D. ; Iranpoor , N. ; Rezaeifard , A. Simple and highly efficient synthesis of oxaziridines by tetrabutylammonium oxone . Tetrahedron Lett. 2004 , 45 , 631 – 634 .
  • Mohajer , D. ; Rezaeifard , A. Efficient oxygenation of hydrocarbons with tetrabutylammonium monopersulfate catalyzed by manganese meso-tetraphenylporphyrin in the presence of imidazole. Tetrahedron Lett. 2002, 43, 1881–1884.
  • Iranpoor , N. ; Mohajer , D. ; Rezaeifard , A. R. Rapid and highly chemoselective biomimetic oxidation of organosulfur compounds with tetrabutylammonium peroxymonosulfate in the presence of manganese meso-tetraphenylporphyrin and imidazole . Tetrahedron Lett. 2004 , 45 , 3811 – 3815 .
  • Trost , B. M. ; Braslau , R. Tetra-n-butylammonium oxone: Oxidations under anhydrous conditions . J. Org. Chem. 1988 , 53 , 532 – 537 .
  • Boucher , L. J. Manganese Schiff's base complexes (II): Synthesis and spectroscopy of chloro-complexes of some derivatives of (salicylaldehydeethylenediimato)manganese(III) . J. Inorg. Nucl. Chem. 1974 , 36 , 531 – 536 .
  • (a) Srinivasa , K. ; Michaud , P. ; Kochi , J. K. Epoxidation of olefins with cationic (salen)Mn(III) complexes: The modulation of catalytic activity by substituents . J. Am. Chem. Soc. 1986 , 108 , 2309 – 2320 ; (b) Rihter , B. ; Masnovi , J. Oxidation of alkynes and ylides by oxo(salen)chromium(V)(salen = N,N′-ethylenebis-salicylideneiminato)trifluoromethane sulphonate . J. Chem. Soc., Chem. Commun. 1988 , 35 – 37 ; (c) Chellamani , A. ; Alhaji , N. M. I. ; Rajagopal , S. ; Sevvel , R. ; Srinivasan , C. Mechanism of oxidation of organic sulphides by oxo(salen)manganese(V) complexes . Tetrahedron 1995 , 51 , 12677 – 12698 ; (d) Chellamani , A. ; Alhaji , N. M. I. ; Rajagopal , S. Applicability and mathematical verification of the reactivity–selectivity principle in the oxidation of thioanisoles by oxo(salen)manganese(V) complexes . J. Chem. Soc., Perkin. Trans. 2 1997 , 299 – 302 ; (e) Koola , J. ; Kochi , J. K. Nickel catalysis of olefin epoxidation . Inorg. Chem. 1987 , 26 , 908 – 916 ; (f) Chen , D. ; Martell , A. E. Dioxygen affinities of synthetic cobalt Schiff base complexes . Inorg. Chem. 1987 , 26 , 1026 – 1030 ; (g) Trivedi , B. M. ; Bhattacharya , P. K. ; Ganeshpure , P. A. ; Satish , S. Epoxidation of olefins catalysed by Mn(III)-Schiff base complexes . J. Mol. Cat. 1992 , 5 , 109 – 115 .
  • (a) Collman , P. J. ; Zeng , L. ; Brauman , I. J. Donor ligand effect on the nature of the oxygenating species in Mn(III)(salen)–catalyzed epoxidation of olefins: Experimental evidence for multiple active oxidants . Inorg. Chem. 2004 , 43 , 2672 – 2679 ; (b) Gross , Z. ; Ini , S. Remarkable effects of metal, solvent, and oxidant on metalloporphyrin-catalyzed enantioselective epoxidation of olefins . J. Org. Chem. 1997 , 62 , 5514 – 5521 .
  • Ortiz de Montellano , P. R. ; Beilan , H. S. ; Kunze , K. L. N-Alkylprotoporphyrin IX formation in 3,5-dicarbethoxy-1,4-dihydrocollidine treated rats: Transfer of the alkyl group from the substrate to the porphyrin . J. Biol. Chem. 1981 , 256 , 6708 – 6713 .
  • Adibi , H. ; Hajipour , A. R. 1,4-Dihydropyridines using benzyltriphenylphosphonium peroxymonosulfate under almost neutral reaction conditions . Bioorg. Med. Chem. Lett. 2007 , 17 , 1008 – 1012 .
  • Liu , Z. ; Yu , W. ; Yang , L. ; Liu , Z.-L. A novel oxidation–ring contraction of Hantzsch 1,4-dihydropyridines to polysubstituted furans . Tetrahedron Lett. 2007 , 48 , 5321 – 5324 .

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