Unmasking of aminoanthroquinone moiety through a ring opening in the presence of copper salts and a subsequent cross-coupling/recyclization cascade

S. F. Vasilevsky, L. M. Gornostaev, A. A. Stepanov, E. V. Arnold, I. V. Alabugin

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

In the presence of copper(I) salts, 3-bromo- or 3-iodoisoxazoles undergo isoxazole ring opening to give keto amines that can undergo further one-pot cascade cross-coupling/recyclization transformation into an extended flat polyaromatic ring system that can provide an interesting new platform for the design of DNA intercalators. If necessary, the three-step reaction cascade can be interrupted at a desired intermediate step through a judicious choice of reaction temperature and catalyst.

Original languageEnglish
Pages (from-to)1867-1870
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number10
DOIs
Publication statusPublished - 5 Mar 2007
Externally publishedYes

Fingerprint

Intercalating Agents
Isoxazoles
Amines
Copper
Salts
Catalysts
Temperature
DNA

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Unmasking of aminoanthroquinone moiety through a ring opening in the presence of copper salts and a subsequent cross-coupling/recyclization cascade. / Vasilevsky, S. F.; Gornostaev, L. M.; Stepanov, A. A.; Arnold, E. V.; Alabugin, I. V.

In: Tetrahedron Letters, Vol. 48, No. 10, 05.03.2007, p. 1867-1870.

Research output: Contribution to journalArticle

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