Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide

Hiroki Tanimoto*, Ryo Adachi, Aoi Otsuki, Takenori Tomohiro

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

We studied the hydrazide compounds of the α-azidoacetyl group, which showed specific click reactivity by the intramolecular hydrogen bonding between the azido group and the N-H of the hydrazide moiety. In the competitive click reactions with a general alkyl azide, both traceless and non-traceless Staudinger-Bertozzi ligation occurred azide-site-selectively by the acceleration effect of the hydrogen bonding. However, the product obtained from the traceless reaction was further transformed into heterocyclic compounds. In addition, in an attempt at a synthesis of naphthalimide-possessing azidoacetyl hydrazide, nitrogen-nitrogen bond cleavage of the azidoacetyl hydrazides occurred to give the reduced amine product. These unexpected results could help design molecules for the successful Staudinger-Bertozzi ligation of the hydrazide compounds and develop a new nitrogen-nitrogen bond cleavage method.

Original languageEnglish
Pages (from-to)520-533
Number of pages14
JournalOrganics
Volume3
Issue number4
DOIs
StatePublished - 2022/12

Keywords

  • click chemistry
  • hydrogen-bonding interaction
  • nitrogen-nitrogen bond cleavage
  • organic azides
  • staudinger ligation

ASJC Scopus subject areas

  • Organic Chemistry

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