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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 6
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Original Articles

Mono‐nitration of Coumarins by Nitric Oxide

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Pages 985-992 | Received 25 Jul 2003, Published online: 21 Aug 2006

References

  • Finn , G. J. , Kenealy , E. , Creaven , B. S. and Egan , D. A. 2002 . In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines . Cancer Lett. , 183 : 61 [PUBMED] [INFOTRIEVE] [CSA]
  • El‐Sayed , A. M. , Ghattas , A. G. , El‐Wassimy , M. T. and Allah , O. A.A. 1999 . Synthesis of some new biologically‐active coumarin derivatives . Farmaco , 54 : 56 [CROSSREF]
  • Oketch‐Rabah , H. A. , Mwangi , J. W. , Lisgarten , J. and Mberu , E. K. 2000 . A new antiplasmodial coumarin from Toddalia asiatica roots . Fitoterapia , 71 : 636 [CSA] [CROSSREF]
  • Majumdar , K. C. and Ghosh , S. K. 1994 . Studies on amine oxide rearrangements: regioselective synthesis of pyrano(3,2‐e) indol‐7‐one . J. Chem. Soc. Perkin Trans. 1 , : 2889 [CROSSREF]
  • Majumdar , K. C. and Biswas , P. 1999 . Synthesis of bioreactive heterocycles:one pot regioselective synthesis of pyrano[3,2-f]benzo[b]thiophene derivatives . Tetrahedron , 55 : 1449 [CROSSREF]
  • Huebner , C. F. and Link , K. P. 1945 . Studies on 4-hydroxycoumarin. VII. Reactions of 4-hydroxycoumarin with cationoid reagents . J. Am. Chem. Soc. , 67 : 99
  • Banerji , A. and Nandi , G. 1987 . Metal reagents in organic reactions: part V reactions of coumarins with thallium III salt . Heterocycles , 26 ( 5 ) : 1221
  • Ganguly , N. , Sukai , A. K. and De , S. 2001 . Cerium (IV) ammonium nitrate mediated nitration of coumarins . Synthetic Commun. , 31 ( 2 ) : 301 [CROSSREF]
  • Mori , T. and Suzuki , H. 1995 . Ozone-mediated nitration of aromatic compounds with lower oxides of nitrogen (the Kyodai‐nitration) . Synlett. , : 383 [CROSSREF]
  • Bosch , E. and Kochi , J. K. 1994 . Thermal and photochemical nitration of aromatic hydrocarbons with nitrogen dioxide . J. Org. Chem. , 59 : 3314
  • Riebsomer , J. L. 1945 . The reactions of nitrogen tetroxide with organic compounds . Chem. Rev. , 36 : 157
  • Brunton , G. , Cruse , H. W. , Riches , K. M. and Whittle , A. 1979 . On the mechanism of nitration of 4-methyl-2,6-ditertiarybutylphenol by nitrogen dioxide in the liquid phase . Tetrahedron Lett. , 20 : 1093 [CROSSREF]
  • Fischer , A. and Mathivanan , N. 1988 . Formation of dienones on the reaction of cresols, xylenols, and 2-naphthol with nitrogen dioxide: observation of keto tautomers of nitrophenols . Tetrahedron Lett. , 29 : 1869 [CROSSREF]
  • Coombes , R. G. , Hadjigeorgiou , P. , Jensen , D. G.J. and Morris , D. L. 1996 . Nitration: Recent Laboratory and Industrial Development , ACS Symposium Series 623 Edited by: Albright , L. F. , Carr , R. V.C. and Schmitt , R. J. American Chemical Society . Chap. 3
  • Moncada , S. , Palmer , R. M. and Higgs , E. A. 1991 . Nitric oxide: physiology, and pharmacology . Pharmacol. Rev. , 43 : 109 [PUBMED] [INFOTRIEVE]
  • Galla , H. J. 1993 . Nitric oxide, NO, and intercellular messenger . Angew. Chem. Int. Ed. Engl. , 32 : 378 [CROSSREF]
  • Janzen , E. G. , Wilcox , A. L. and Manoharon , V. 1993 . Reaction of nitric oxide with phenolic antioxidants and phenooxyl radicals . J. Org. Chem. , 58 : 3597
  • Wilcox , A. W. and Janzen , E. G. 1993 . Nitric oxide reaction with antioxidants in model systems: sterically hindered phenols and α‐tocopherol in sodium dodecyl sulfate (SDS) micelles . J. Chem. Soc. Chem. Commun. , : 1377 [CROSSREF]
  • Yenes , S. and Messeguer , A. 1999 . A study of the reaction of different phenol substrates with nitric oxide and peroxynitrite . Tetrahedron , 55 : 14111 [CROSSREF]
  • Suzuki , T. , Yamaoka , R. , Nishi , M. , Ide , H. and Makino , K. 1996 . Isolation and characterization of a novel product, 2′-deoxyguanosine, oligodeoxynucleotide, and calf thymus DNA treated by nitrous acid and nitric oxide . J. Am. Chem. Soc. , 118 : 2515 [CROSSREF]
  • Itoh , T. , Nagata , K. , Mastuya , Y. , Miyazaki , M. and Ohsawa , A. 1997 . Reaction of nitric oxide with amines . J. Org. Chem. , 62 : 3582 [CROSSREF]
  • Wu , L. M. , Chen , W. and Liu , Z. L. 2001 . Stable free radicals generated during the oxidation of 4-alkyl Hantzsch 1,4-dihydropyridines with nitrosonium – EPR evidence . Res. Chem. Intermed. , 27 ( 3 ) : 219 [CROSSREF]
  • Mukaiyama , T. , Hata , E. and Yamada , T. 1995 . Convenient and simple preparation of nitroolifens niytration of olifens with nitric oxide . Chem. Lett. , : 505
  • Nagano , T. , Takizawa , H. and Hirobe , M. 1995 . Reaction of nitric oxide with dioxygen . Tetrahedron Lett. , 36 : 8239
  • Kelly , D. R. , Jones , S. , Adigun , J. O. , Kon , K. S.V. and Jackson , S. K. 1997 . The addition of nitric oxide to 2,5-dimethyl-hexa-2,4-diene gives nitrogen dioxide adducts . Tetrahedron Lett. , 38 : 1245 [CROSSREF]
  • Zhu , X. Q. , Xian , M. , Wang , K. and Cheng , J. P. 1999 . Is NO (nitric oxide) an electron acceptor or an electrophile? A detailed thermodynamic investigation on the mechanism of NO‐initiated reactions with 3,6-dibromocarbazolide anion and related carbanion . J. Org. Chem. , : 4187 [CROSSREF]
  • Thompson , M. J. and Zeegers , P. J. 1990 . Studies on the two‐phase nitration of phenols (part 2) . Tetrahedron , 46 : 2661 [CROSSREF]
  • Degraw , J. I. and Tsakotellis , P. 1969 . A convenient synthesis of 6-hydroxy coumarins . J. Chem. Eng. Data. , 14 : 509
  • Ren , X. F. , Chen , X. C. , Peng , K. , Xie , X. G. , Xia , Y. M. and Pan , X. F. 2002 . First enatioselective synthesis of daphneticin and its regioisomer . Tetrahedron: Asymmetry , 13 : 1799 [CROSSREF]

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