N, N-bis(quinonyl)amines; synthesis and X-ray structure

Shmuel Bittner, Chandran Meenakshi, Galina Temtsin

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

The preparation of several symmetrical and nonsymmetrical N, N-bis(quinonyl)amines is reported. These compounds, which have two quinones separated by one amino group, were obtained by an unexpected reaction of primary or secondary substituted aminoquinones. While not nucleophilic enough to react with simple electrophiles, these aminoquinones did react with haloquinones and also with unsubstituted quinones under very mild conditions to afford diquinonylamines in average to good yields. These vinylogous quinone-imides were characterized using common spectroscopic methods as well as X-ray crystallography.

Original languageEnglish
Pages (from-to)7423-7429
Number of pages7
JournalTetrahedron
Volume57
Issue number34
DOIs
StatePublished - 20 Aug 2001

Keywords

  • Aminoquinones
  • Michael reaction
  • Quinones
  • X-ray crystal structure

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'N, N-bis(quinonyl)amines; synthesis and X-ray structure'. Together they form a unique fingerprint.

Cite this