- Mechanistic study of electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline in aqueous solutions: hydrolysis, trimerization, and hydroxylation processes
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Abstract The electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline has been studied in various pHs using cyclic voltammetry and controlled potential coulometry. The results indicate that the electrochemically generated p-quinonediimine participate
- Beiginejad, Hadi,Nematollahi, Davood
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- A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26
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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.
- Yu, Wanwan,Hjerrild, Per,Jacobsen, Kristian M.,Tobiesen, Henriette N.,Clemmensen, Line,Poulsen, Thomas B.
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supporting information
p. 9805 - 9809
(2018/07/31)
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- Electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline in aqueous solutions
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Electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline (1) has been studied at various pH values using cyclic voltammetry and controlled-potential coulometry. The results indicate that electrochemically generated p-benzoquinonediimine (1ox) is unstable and participates in the two types of reactions based on solution's pH. The results also show that in the acidic media, electrochemically generated 1ox via two successive hydrolysis reactions is converted to 2,5-diethoxy-p-benzoquinone (3ox), while at intermediate pH values, the Michael addition reaction of 1-1ox takes place prior to the hydrolysis reaction. Our data show that in these pH values, 1ox via two successive Michael addition reactions followed by a hydrolysis reaction is converted to 2,5-bis(2,5-diethoxy-4-morpholinophenylamino)-3,6-diethoxy-p- benzoquinone (6ox).
- Beiginejad, Hadi,Nematollahi, Davood
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p. 242 - 250
(2013/12/04)
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- Rearrangement of allyl aryl ethers III1 reaction of alkoxyhydroquinone with cycloalkenediols
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Cycloalkenobezofurans 5a-d were prepared in one-pot reaction from methoxyhydroquinone, 2,6- and 2,3-dialkoxyhydroquinone (1) with cycloalkenediol (2). Reaction between the isomeric 2,5-dialkoxyhydroquinones (9) with diol 2 led to the formation of monoalkoxybenzofurans 5d-g with the loss of an alkoxy group.
- Novak, Lajos,Kovacs, Peter,Pirok, Gyoergy,Kolonits, Pal,Hanania, Michel,Donath, Katalin,Szantay, Csaba
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p. 9789 - 9798
(2007/10/03)
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