superacid-induced reactions of nefopamsuperacid-induced nefopam的反应.pdfVIP

Hindawi Publishing Corporation Organic Chemistry International Volume 2010, Article ID 496818, 5 pages doi:10.1155/2010/496818 Research Article Superacid-Induced Reactions of Nefopam Larecia Knoecer, Daniel DeSchepper, and Douglas A. Klumpp Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA Correspondence should be addressed to Douglas A. Klumpp, dklumpp@ Received 10 November 2009; Revised 13 February 2010; Accepted 16 March 2010 Academic Editor: Cyril Parkanyi Copyright © 2010 Larecia Knoecer et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The analgesic drug nefopam reacts in superacidic media to form a dicationic superelectrophiles by ring opening. The dication species is capable of reacting with arenes in Friedel-Crafts-type conversions. This chemistry is used to prepare novel derivatives of nefopam. During the 1970s, Olah and coworkers proposed the concept The degradation of nefopam (1) under stressed storage of superlectrophilic activation [1]. Those seminal reports conditions (90◦C in alkaline, pH 9.0, and acidic, pH 2.0, prompted many subsequent investigations of dicationic media) was studied by Wang and coworkers [ 11]. Among electrophilic species and superelectrophiles [2]. Superelec- their observations, it was reported that the acidic conditions trophiles may arise from the interaction of cationic elec- promoted ether cleavage to the diol (4, Scheme 1) along trophiles with acidic media, as in the protonation of the with other