Intramolecular cyclization with nitrenium ions generated by treatment of N-Acylaminophthalimides with hypervalent iodine compounds: formation of lactams and spiro- …

Y Kikugawa, A Nagashima, T Sakamoto…

Index: Miyazawa, Etsuko; Sakamoto, Takeshi; Kikugawa, Yasuo Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1998 , # 1 p. 7 - 12

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Citation Number: 73

Abstract

N-Phthalimido-N-acylnitrenium ions are generated from N-acylaminophthalimides, a new class of precursors, by treatment with hypervalent iodine compounds (PIFA and HTIB). In HFIP, the nitrenium ions undergo intramolecular electrophilic substitution reactions to afford N-aminonitrogen heterocycles in high yields. In TFEA, spirodienones bearing the 1-azaspiro [4.5] decane skeleton are obtained by treatment of N-phthalimido-3-(4-halogenophenyl) ...