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Esterification‐nitration of Ortho ‐hydroxyphenyl Carboxylic Acids and Benzoic Acids with Cerium(IV) Ammonium Nitrate (CAN)
Author(s) -
Pan WenBin,
Wei LiMei,
Wei LiLan,
Wu ChinChung,
Wu YangChang
Publication year - 2005
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200500027
Subject(s) - chemistry , nitration , cerium , nitrate , ammonium nitrate , cerium nitrate , organic chemistry , benzoic acid , ammonium
Abstract A convenient and useful esterification was realized, and this reaction proceeded without a dehydrating reagent or water removal equipment. A series of ortho ‐hydroxyphenyl carboxylic acids and benzoic acids were transformed to their corresponding methyl esters under CAN/CH 3 OH reaction conditions. Whereas in an aprotic solvent, acetonitrile, sp 3 ‐C tethered ortho ‐hydroxyphenyl carboxylic acids undergo simultaneous o , p ‐dinitration and intramolecular esterification reactions in good yields. Also, 2‐((1 E )‐2‐nitrovinyl)‐4‐nitro‐phenol ( 3e ) showed selective cytotoxicities toward MCF‐7, HEP G2, and HEP 3B cell lines with IC 50 values of 23.50, 7.33, and 7.59 ug/mL, respectively.