6323-02-0Relevant articles and documents
A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26
Yu, Wanwan,Hjerrild, Per,Jacobsen, Kristian M.,Tobiesen, Henriette N.,Clemmensen, Line,Poulsen, Thomas B.
supporting information, p. 9805 - 9809 (2018/07/31)
The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3?2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.
Synthesis and biological evaluation of 2,5-bis(alkylamino)-1,4- benzoquinones
Barbosa, Luiz Claudio Almeida,Pereira, Ulisses Alves,Maltha, Celia Regina Alvares,Teixeira, Robson Ricardo,Valente, Vania Maria Moreira,Ferreira, Jose Roberto Oliveira,Costa-Lotufo, Leticia Veras,Moraes, Manoel Odorico,Pessoa, Claudia
experimental part, p. 5629 - 5643 (2010/12/24)
A series of twelve 2,5-bis(alkylamino)-1,4-benzoquinones were prepared in yields ranging from 9-58% via the reaction between p-benzoquinone and various amines. The structures of the synthesized compounds were confirmed by IR, 1H- and 13/s
Probing Delocalization across Alkyne-Containing Linkages: Synthesis and Cyclic Voltammetry of Bridged Phenylenediamines
Zhou, Qin,Swager, Timothy M.
, p. 7096 - 7100 (2007/10/03)
This paper presents the synthesis of N,N,N',N'-tetraethyl-1,4-phenylenediamines bridged by ethynyl-phenyl-ethynyl and diethynyl linkages.These compounds are of interest to determine if the N,N,N',N'-tetraethyl-1,4-phenylenediamines exhibit delocalized mixed oxidation states when oxidized electrochemically. 1-Butoxy-2,5-bis(N,N-diethylamino)-4-ethynylbenzene was a key intermediate, and nucleophilic addition of lithium (trimethylsilyl)acetylide to 2,5-bis(N,N-diethylamino)-1,4-benzoquinone provided an efficient synthesis of this compound.This intermediate was then assembled into the redox assemblies of interest in high yield by use of palladium-catalyzed cross-coupling and copper-catalyzed oxidative homo-coupling protocols.Cyclic voltammetry of these compounds indicate that the N,N,N',N'-tetraethyl-1,4-phenylenediamine redox units behave independently and that the interactions are principally electrostatic.As a result, we conclude that the electrochemically generated radical cations and dications are highly localized.
Aryl Nitrenes from N,N'-Diarylbenzoquinone Di-imine N,N'-Dioxides and N-Arylbenzoquinone Imine N-Oxides
Forrester, Alexander R.,Ogilvy, Munro M.,Thomson, Ronald H.
, p. 2023 - 2026 (2007/10/02)
Photolyses of the title quinone imine N.oxides give mainly azoarenes formed by dimerisation of triplet aryl nitrenes.
