Synthesis and Reactions of Iodo Lactams

Spencer Knapp, Anthony T. Levorse

Research output: Contribution to journalArticle

125 Scopus citations

Abstract

The synthesis of a series of iodo lactams has been achieved by a new cyclization method that depends on generating N,O-bis(trimethylsilyl)imidate derivatives as intermediates. Treatment of an unsaturated amide with trimethylsilyl triflate in pentane and then iodine in tetrahydrofuran gives the iodo lactam. Some reactions of this new difunctional group with bases, nucleophiles, and Michael acceptors leading to functionalized or elaborated lactams are presented. In general, iodo lactams undergo direct SN2 reactions with reactive (but weakly basic) nucleophiles like azide and triphenylphosphine and elimination or decomposition in the presence of bases or basic nucleophiles. Sodium hydride may be used to generate an N-acylaziridine intermediate, which can be opened with azide to deliver an azido lactam with overall retention of stereochemistry. Silver-assisted solvolysis of iodo lactams gives the hydroxy lactams with retention of configuration, probably also because of participation by the lactam nitrogen. The sodium salt of 5-(iodomethyl)-2-pyrrolidinone (3), generated at -20 °C, undergoes an annulation reaction with unsaturated esters (but not sulfones), leading to pyrrolizidine derivatives.

Original languageEnglish (US)
Pages (from-to)4006-4014
Number of pages9
JournalJournal of Organic Chemistry
Volume53
Issue number17
DOIs
StatePublished - Jan 1 1988

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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