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April 6, 2026Organic Letters2 citations

Radical Haloazidation of 1,5-Enenitriles for Making N -Haloimines and Sequential Triazolation to Form Tricyclics

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XMXiaoming MaMYMifei YuZGZijie Gao

Key Points

  • This research aims to develop a novel method for synthesizing N-haloimines using radical haloazidation of 1,5-enenitriles.
  • Utilized Mn-catalyzed radical haloazidation with TMSN3 and N-halosuccinimides.
  • Engaged azido N-haloimines in diannulation with alkynes.
  • Applied cascade CuAAC and intramolecular electrophilic aromatic substitution.
  • Successfully synthesized azido N-haloimines.
  • Produced triazole-fused heterocycles through the outlined method.
  • Demonstrated a new approach to organic synthesis with potential applications.

Abstract

A new method for making N-haloimines by Mn-catalyzed radical haloazidation of 1,5-enenitriles with TMSN3 and N-halosuccinimides is introduced. The resulting azido N-haloimines are used for diannulation with alkynes to form triazole-fused heterocycles via a cascade CuAAC with alkynes and intramolecular electrophilic aromatic substitution (EAS).

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Cite This Study

Ma et al. (2026) studied this question.

synapsesocial.com/papers/69d34e1e9c07852e0af979d8https://doi.org/10.1021/acs.orglett.6c00773
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