- Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
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An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
- Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
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supporting information
p. 2298 - 2302
(2021/04/05)
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- Regioselective gold-catalyzed oxidative C-N bond formation
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A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic aromatic metalation patterns.
- Marchetti, Louis,Kantak, Abhishek,Davis, Riley,Deboef, Brenton
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supporting information
p. 358 - 361
(2015/01/30)
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- HYDROLYSIS OF 1-OXO-3-ETHYL-4-ARYL-2,3-BEZOXAZINIUM SALTS
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Irrespective of the character of the substituent at position 4, the action of triethyloxonium fluoroborate on 1-oxo-4-aryl(methyl)-2,3-benzoxazines leads to the formation of 1-oxo-3-ethyl-4-aryl(methyl)-2,3-benzoxazinium tetrafluoroborates, which readily exchange the anion, being converted into the corresponding perchlorates and tetrachloroferrates.Hydrolysis of the oxobenzoxazinium perchlorates leads to 4-hydroxy-3-ethyl-4-aryl(methyl)-2,3-benzoxazin-1-ones, which exhibit the characteristics of carbinol bases.The formation of N-arylphthalimides is also observed in the case of the oxobenzoxazinium salts containing accepting or weakly don ating substituents.
- Volynets, N. F.,Samartseva, I. V.,Pavlova, L. A.
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p. 574 - 577
(2007/10/02)
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- Process for the production of cyclic carboxylic acid imides
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In a process for reacting an aromatic or hydroaromatic alicyclic or heterocyclic dicarboxylic acid or its anhydride with an aliphatic or aromatic alicyclic or heterocyclic mono- or di-amine to produce an N-substituted dicarboxylic acid imide with a splitting off of water, the improvement of carrying out the reaction in a liquid solvent mixture consisting essentially of a non-polar organic solvent and a strongly polar organic solvent which together form a ternary azeotrope with water at reaction temperatures between about 40°C. and 160°C. The imide products are generally known for use as intermediates and final products in a number of industries.
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