Synthesis of Carboxy ATTO 647N Using Redox Cycling for Xanthone Access

Org Lett. 2020 Jan 17;22(2):381-385. doi: 10.1021/acs.orglett.9b03981. Epub 2019 Dec 11.

Abstract

A synthesis of the carbopyronine dye Carboxy ATTO 647N from simple materials is reported. This route proceeds in 11 forward steps from 3-bromoaniline with the key xanthone intermediate formed using a new oxidation methodology. The step utilizes an oxidation cycle with base, water, iodine, and more than doubles the yield of the standard permanganate oxidation methodology, accessing gram-scale quantities of this late-stage product. From this, Carboxy ATTO 647N was prepared in only four additional steps. This facile route to a complex fluorophore is expected to enable further studies in fluorescence imaging.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Pyronine / chemical synthesis*
  • Pyronine / chemistry
  • Xanthones / chemistry*

Substances

  • Fluorescent Dyes
  • Xanthones
  • xanthone
  • Pyronine