Affordable Access

Publisher Website

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.

There are no comments yet on this publication. Be the first to share your thoughts.

Statistics

Seen <100 times
0 Comments