Esterification‐nitration of  Ortho ‐hydroxyphenyl Carboxylic Acids and Benzoic Acids with Cerium(IV) Ammonium Nitrate (CAN) | Zendy

Pan WenBin | Zendy; Wei LiMei | Zendy; Wei LiLan | Zendy; Wu ChinChung | Zendy; Wu YangChang | Zendy

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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

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.

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