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Paper | Regular issue | Vol 75, No. 5, 2008, pp.1133-1149
Published online, 25th January, 2008
DOI: 10.3987/COM-07-11295
Synthesis of Nitrogen Heterocycles by Intramolecular Cyclization of Alkenyl N-Acylaminophthalimides Using Phenyliodine(III) Bis(trifluoroacetate) (PIFA)

Masato Tsukamoto, Kousuke Murata, Takeshi Sakamoto, Setsuo Saito,* and Yasuo Kikugawa*

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

Abstract

PIFA-mediated intramolecular cyclization of alkenyl N-acylaminophthalimides leads to the formation of a new C-N bond via an N-acyl-N-phthalimidonitrenium ion intermediate. The reaction pathway also results in the introduction of an oxygen function into the molecule giving added versatility to this single step procedure.