Photochemical synthesis of medium-ring azalactams from N-(aminoalkyl)-2-stilbenecarboxamides

Frederick D. Lewis*, Steven G. Kultgen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The photochemical reactions of several N-(aminoalkyl)-2-stilbenecarboxamides have been investigated. The amine groups quench the stilbenecarboxamide fluorescence intensity, presumably via intramolecular electron transfer. The relatively low quenching efficiencies and the absence of intramolecular exciplex formation are attributed to the molecular structure which prevents effective overlap between the stilbene and amine chromophores. The secondary amines are observed to undergo regioselective intramolecular addition to afford 9-or 10-ring azalactams in 25-43% isolated yield. The dependence of both fluorescence quenching and adduct formation upon molecular structure are discussed.

Original languageEnglish (US)
Pages (from-to)159-164
Number of pages6
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume112
Issue number2-3
DOIs
StatePublished - Jan 31 1998

Keywords

  • Azalactams
  • N-(aminoalkyl)-2-stilbenecarboxamides
  • Photochemical synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

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