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

作者: Nemai C. Ganguly , Mrityunjoy Datta , Prithwiraj De , Romaprosad Chakravarty

DOI: 10.1081/SCC-120015821

关键词:

摘要: 6-Hydroxycoumarins and their O-methyl ethers were selectively nitrated in the carbocyclic ring even presence of activating 4-Me group 2-pyrone with cerium(IV) ammonium nitrate (CAN) acetic acid acetonitrile acceptable-to-excellent yields. Acetonitrile was found to be a better solvent for regioselective nitration than acid. Use CAN on montmorillonite K-10 clay under microwave irradiation expeditious solvent-free has been revealed first time.

参考文章(27)
Ripudaman Malhotra, George Andrew Olah, Subhash C. Narang, Nitration: Methods and Mechanisms ,(1989)
G. R. Desiraju, Organic solid state chemistry Elsevier Science. ,(1987)
Dan Amir, Elisha Haas, Reduced bovine pancreatic trypsin inhibitor has a compact structure. Biochemistry. ,vol. 27, pp. 8889- 8893 ,(1988) , 10.1021/BI00425A003
Keith Smith, Karl Fry, Michael Butters, Barry Nay, Para-selective mononitration of alkylbenzenes under mild conditions by use of benzoyl nitrate in the presence of a zeolite catalyst Tetrahedron Letters. ,vol. 30, pp. 5333- 5336 ,(1989) , 10.1016/S0040-4039(01)93779-7
K Tanaka, F Toda, Solvent-free organic synthesis ,(2003)
Rajender S. Varma, Kannan P. Naicker, Per J. Liesen, Selective nitration of styrenes with clayfen and clayan: A solvent-free synthesis of β-nitrostyrenes Tetrahedron Letters. ,vol. 39, pp. 3977- 3980 ,(1998) , 10.1016/S0040-4039(98)00740-0
Tomasz Miłczak, Jarosław Jacniacki, Janusz Zawadzki, Monika Malesa, Wincenty Skupiński, NITRATION OF AROMATIC COMPOUNDS ON SOLID CATALYSTS Synthetic Communications. ,vol. 31, pp. 173- 187 ,(2001) , 10.1081/SCC-100000197
B. M. Choudary, M. Sateesh, M. Lakshmi Kantam, K. Koteswara Rao, K. V. Ram Prasad, K. V. Raghavan, J. A. R. P. Sarma, Selective nitration of aromatic compounds by solid acid catalysts Chemical Communications. pp. 25- 26 ,(2000) , 10.1039/A908011B
Enrico Baciocchi, Sandro Mei, Cesare Rol, Luigi Mandolini, Oxidation of aromatic compounds by metal ions. 5. Oxidative acetoxylation of anisole by ceric ammonium nitrate in acetic acid Journal of Organic Chemistry. ,vol. 43, pp. 2919- 2921 ,(1978) , 10.1021/JO00408A039
Lionel Delaude, Pierre Laszlo, Keith Smith, Heightened selectivity in aromatic nitrations and chlorinations by the use of solid supports and catalysts Accounts of Chemical Research. ,vol. 26, pp. 607- 613 ,(1993) , 10.1021/AR00036A001