Studies on Regioselectivity of Nitration of Coumarins with Cerium(IV) Ammonium Nitrate: Solid-State Nitration of 6-Hydroxy-Coumarins on Montmorillonite K-10 Clay Support Under Microwave Irradiation

References

• Olah , G.A. , Malhotra , R. and Narang , S.C. 1989 . Nitration Methods and Mechanism 5 – 15 . New York : VCH .
   Google Scholar
• Schofield , K. 1980 . Aromatic Nitration Cambridge : Cambridge University Press .
   Google Scholar
• Strazzolini , P. , Giumanini , A.G. , Runcio , A. and Scuccato , M. 1998 . Experiments on the Chaperon effect in the nitration of aromatics . J. Org. Chem. , 63 : 952 – 958 .
   Google Scholar
• Strazzolini , P. , Verardo , G. , Gorassini , F. and Giumanini , A.G. 1995 . Orientation effect of side chain substituents in aromatic substitution induced ortho nitration . Bull. Chem. Soc. Jpn. , 68 : 1155 – 1161 .
   Google Scholar
• Chaudhary , B.M. , Sateesh , M. , Lakshmikantam , M. , Rao , K.K. , Ram Prasad , K.V. , Raghavan , K.V. and Sarma , J.A.R.P. 2000 . Selective nitration of aromatic compounds by solid acid catalysts . J. Chem. Soc., Chem. Commun. , : 25 – 26 .
   Google Scholar
• Delaude , L. , Laszlo , P. and Smith , K. 1993 . Heightened selectivity in aromatic nitrations and chlorinations by the use of solid supports and catalysts . Acc. Chem. Res. , 26 : 607 – 613 .
   Web of Science ®Google Scholar
• Smith , K. , Fry , K. , Butters , M. and Nay , B. 1989 . Para-Selective mononitration of alkylbenzenes under mild conditions by use of benzoyl nitrate in the presence of zeolite catalyst . Tetrahedron Lett. , 30 : 5333 – 5336 .
   Web of Science ®Google Scholar
• Kwok , T.J. , Jayasuriya , K. , Reddy , D. and Brodman , B.W. 1994 . Application of H-ZSM-5 zeolite for regioselective mononitration of toluene . J. Org. Chem. , 59 : 4939 – 4942 .
   Web of Science ®Google Scholar
• Olah , G.A. , Malhotra , R. and Narang , S.C. 1978 . Aromatic substitution. 43. Perfluorinated resinsulfonic acid catalyzed nitration of aromatics . J. Org. Chem. , 43 : 4628 – 4632 .
   Web of Science ®Google Scholar
• Verma , R.S. , Naicker , K.P. and Liesen , P. 1998 . Selective nitration of styrenes with clayfen and clayan: a solvent-free synthesis of β-nitrostyrenes . Tetrahedron Lett. , 39 : 3977 – 3980 .
   Google Scholar
• Milczak , T. , Jacniacki , J. , Zawadzki , J. , Malesa , M. and Skupinski , W. 2001 . Nitration of aromatic compounds on solid catalysts . Synth. Commun. , 31 : 173 – 187 .
   Web of Science ®Google Scholar
• Ganguly , N. , Sukai , A.K. and De , S. 2001 . Cerium(IV) ammonium nitrate mediated nitration of coumarins . Synth. Commun. , 31 : 301 – 309 .
   Web of Science ®Google Scholar
• Sun , W.-C. , Gee , K.R. and Haugland , R.P. 1998 . Synthesis of novel fluorinated coumarins: excellent UV-light excitable fluoroscent dyes . Bioorg. Med. Chem. Lett. , 8 : 3107 – 3110 .
   Google Scholar
• Amir , E. and Hass , E. 1998 . Reduced bovine pancreatic trypsin inhibitor has a compact structure . Biochemistry , 27 : 8889 – 8893 .
   Google Scholar
• Adronov , A. and Fréchet , J.M.J. 2000 . Light-harvesting dendrimers . J. Chem. Soc., Chem. Commun. , : 1701 – 1710 .
   Google Scholar
• Adronov , A. , Gilat , S.L. , Fréchet , J.M.J. , Ohta , K. , Neuwahl , F.V.R. and Fleming , G.R. 2000 . Light harvesting and energy transfer in laser-dye-labeled poly(aryl ether) dendrimers . J. Am. Chem. Soc. , 122 : 1175 – 1185 .
   Web of Science ®Google Scholar
• Sethna , S. and Phadke , R. 1953 . “ The pechmann reaction ” . In Organic Reactions Edited by: Adams , R. Vol. 7 , 46 New York : John Wiley & Sons, Inc. . For preparation of 6-hydroxy-4-methylcoumarin, see
   Google Scholar
• Seebach , D. 1990 . Organic Synthesis—Where now? . Angew. Chem. Int. Ed. Engl. , 29 : 1320 – 1367 .
   Web of Science ®Google Scholar
• Toda , F. 1995 . Solid State organic chemistry: efficient reactions, remark-able yields, and stereoselectivity . Acc. Chem. Res. , 28 : 480 – 486 .
   Web of Science ®Google Scholar
• Tanaka , K. and Toda , F. 2000 . Solvent-free organic synthesis . Chem. Rev. , 100 : 1025 – 1074 .
   PubMed Web of Science ®Google Scholar
• Sarma , J.A.R.P. , Nagaraju , A. , Majumdar , K.K. , Samuel , P.M. , Das , I. , Roy , S. and McGhie , A.J. 2000 . Solid state nuclear bromination with N-bromosuccinimide. Part 2. Experimental and theoretical studies of reactions with some substituted benzaldehydes . J. Chem. Soc., Perkin Trans 2 , : 1119 – 1123 .
   Google Scholar
• Desiraju , G.R. 1987 . Organic Solid State Chemistry Amsterdam : Elsevier .
   Google Scholar
• Baciocchi , E. , Mei , S. , Rol , C. and Mandolini , L. 1978 . Oxidative acetoxylation of anisole by ceric ammonium nitrate in acetic acid . J. Org. Chem. , 43 : 2919 – 2921 .
   Google Scholar
• Braun , C.E. and Cook , C.D. 1963 . Org. Synth. Coll. Vol. , 4 : 71
   Google Scholar
• Nishiguchi , T. and Asano , F. 1989 . Oxidation of alcohols by Metallic nitrates supported on silica gel . J. Org. Chem. , 54 : 1531 – 1535 .
   Web of Science ®Google Scholar
• Kim , E.K. and Kochi , J.K. 1989 . Oxidative aromatic nitration with charge-transfer complexes of arenes and nitrosonium salts . J. Org. Chem. , 54 : 1692 – 1702 .
   Web of Science ®Google Scholar
• Dinctürk , S. and Ridd , J.B. 1982 . Reactions of cerium(IV) ammonium nitrate with aromatic compounds in acetonitrile. Part 2. Nitration; comparison with reactions of nitric acid . J. Chem. Soc., Perkin Trans. 2 , 8 : 965 – 969 .
   Google Scholar
• Eberson , L. and Radner , F. 1989 . Nitration of aromatics via electron transfer. II. On the reaction between naphthalene radical cation and nitrogen dioxide . Acta Chem. Scand., Ser. B , 34 : 739 – 745 .
   Google Scholar
• Jiménez , M.C. , Miranda , M.A. , Soto , J. and Jormos , R. 1994 . Electron transfer oxidation of enol derivatives of 2,3-dihydrobenzopyran-4-ones . Tetrahedron , 50 : 7635 – 7644 .
   Google Scholar
• Clarke , H.T. and Haynes , B. 1975 . A Handbook of Organic Analysis, , 5th Ed. New Delhi : Arnold Publishers (India) .
   Google Scholar
• 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 – 102 .
   Web of Science ®Google Scholar