Platinum-catalyzed dehydroalkoxylation-cyclization cascade via N-O bond cleavage

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Abstract

ortho-Alkynylphenylureas and -acetamides 1, with an alkoxy and aryl group on the nitrogen atom, were subjected to platinum-catalyzed cyclization reactions to afford the corresponding tetracyclic compounds 2, via N-O bond cleavage, in good to excellent yields. For example, N-methoxy-N′-methyl-N′-(2- (pent-1-ynyl)phenyl)-N-phenylurea (1a) was reacted for 12 h in the presence of PtI4 (10 mol%) in 1,4-dioxane at 100 Celsius to afford 5-methyl-12-propylindolo[1,2-c]quinazolin-6(5H)-one (2a) in 93% yield, via an iminium-bound platinum carbenoid intermediate, followed by an aromatic C-H insertion.

Original languageEnglish
Pages (from-to)4198-4199
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number12
DOIs
Publication statusPublished - 2009 Apr 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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