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Synthesis and characterization of a diaziridinium ion. Conversion of 3,4-dihydroisoquinolines to 4,5-dihydro-3H-benzo[2,3]diazepines via a formal N-insertion process

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
70
Identifiers
DOI: 10.1016/j.tet.2014.03.015
Keywords
  • Diaziridinium
  • N-Transfer
  • N-Insertion
  • Diazepine
  • Isoquinoline

Abstract

Abstract A diaziridinium ion has been synthesized in high yield and its structure unambiguously confirmed by X-ray crystal analysis. The predicted N-transfer reactivity with olefins of this species was not observed. Instead, upon heating, the diaziridinium ion underwent ring opening to produce a dihydrobenzodiazepene product in good yield, thus achieving a formal N-insertion of the starting dihydroisoquinoline substrate. This process has been demonstrated on 11 total substrates.

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