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Paper | Special issue | Vol 37, No. 1, 1994, pp.293-301
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S1
Cyclization with Nitrenium Ions Generated from N-Methoxy- or N-Allyloxy-N-chloroamides with Anhydrous Zinc Acetate. Synthesys of N-Hydroxy- and N-Methoxynitrogen Heterocyclic Compounds

Yasuo Kikugawa,* Masahiro Shimada, and Kazuhiro Matsumoto

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japana

Abstract

Electrophilic intramolecular aromatic substitution with an N-methoxy- or an N-allyloxyacylnitrenium ion, generated by treatment of an N-methoxy- or an N-allyloxy-N-chloroamide with anhydrous zinc acetate in nitromethane, leads to formation of a nitrogen heterocyclic compound bearing an N-methoxy- or N-allyloxy group. The latter is readily converted to the corresponding N-hydroxy compound by palladium-catalyzed removal of the allyl group.