Rh(III)-catalyzed C-H amidation of 2-arylindoles with dioxazolones: A route to indolo[1,2-c]quinazolines

Xiaogang Wang, Jin Zhang, Di Chen, Bo Wang, Xiufang Yang, Yangmin Ma, Michal Szostak

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45 Scopus citations

Abstract

Rhodium(III)-catalyzed C-H amidation of 2-arylindoles with dioxazolones for the synthesis of indolo[1,2-c]quinazolines is reported. The reaction is compatible with a wide range of electronically diverse 2-arylindoles and dioxazolones, providing indolo[1,2-c]quinazolines in high to excellent yields. Most notably, the combination of this Rh-catalyzed C-H amidation and intramolecular N-H/N-C(O) cyclization enables the most straightforward direct route to indolo[1,2-c]quinazolines to date. Mechanistic studies and evaluation of antitumor activity of these high value heterocycles are disclosed.

Original languageEnglish (US)
Pages (from-to)7038-7043
Number of pages6
JournalOrganic letters
Volume21
Issue number17
DOIs
StatePublished - Sep 6 2019

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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