80917-23-3Relevant academic research and scientific papers
Synthesis of ortho-Azophenols by Formal Dehydrogenative Coupling of Phenols and Hydrazines or Hydrazides
Esguerra, Kenneth Virgel N.,Lumb, Jean-Philip
, p. 8596 - 8600 (2017)
Azophenols are important chromophores and reagents in organic synthesis, with applications as pigments and molecular switches. Here, we describe a catalytic aerobic process that couples phenols and hydrazines or hydrazides for their synthesis. The key aromatic C?N bond is formed by condensation between the hydrazine or hydrazide and an ortho-quinone, which triggers a redox-isomerization to install the azo-functionality. Notable features include rapid access to highly functionalized azophenols with a range of electronic configurations, including “push–pull” systems, conditions that employ simple, unactivated substrates, occurrence at room temperature using an earth-abundant and commercially available copper catalyst, and production of water as the only stoichiometric byproduct.
METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND
-
Paragraph 0362; 0363; 0364, (2017/03/28)
A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:
