- Copper-catalyzed intermolecular thioamination of maleimides with thiols and formamides: A one-step construction of 3-Amino-4-Thiomaleimides using formamides as nitrogen sources
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A highly efficient copper-catalyzed intermolecular C(sp2)-H thioamination of maleimides with thiols and formamides in the presence of fluoroboric acid is reported using various readily available formamides as nitrogen sources and solvents. A diverse range of 3-Amino-4-Thiomaleimides is obtained with good yields under mild conditions, involving C-N and C-S bond formation. This methodology enriches current C-N and C-S bond formation chemistry and features operational simplicity and excellent functional-group tolerance.
- Yang, Zhen-Hua,Zhu, Jia-Nan,Jin, Ze-Hui,Zheng, Jian,Zhao, Sheng-Yin
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p. 4627 - 4636
(2019/02/01)
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- Three-Component Coupling Reactions of Maleimides, Thiols, and Amines: One-Step Construction of 3,4-Heteroatom-functionalized Maleimides by Copper-Catalyzed C(sp2)?H Thioamination
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A copper-catalyzed intermolecular thioamination of maleimides with thiols and amines has been developed. A diverse range of 3-amino-4-thiomaleimides and 3,4-dihydropyrrolo[3,4-b][1,4]thiazine-5,7(2H,6H)-diones were obtained with good yields, involving C?N and C?S bond formations. This methodology is very practical and features high atom economy, excellent functional group tolerance. (Figure presented.).
- Yang, Zhen-Hua,Tan, Hong-Ru,An, Yu-Long,Zhao, Yu-Wei,Lin, Hao-Peng,Zhao, Sheng-Yin
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supporting information
p. 173 - 179
(2017/11/22)
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- Cu/Ag-Cocatalyzed Aerobic Oxidative Amination and CuCl2-Mediated Aerobic Oxidative Chloroamination of Maleimides
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An efficient Cu(OAc)2/Ag2CO3-cocatalyzed approach for the synthesis of 3-aminomaleimides and 3-amino-4-indolylmaleimides has been developed with satisfactory yields. A series of primary and secondary amines are compatible with this reaction. In addition, treatment of maleimides with primary amines using 1 equiv. of CuCl2leads to the formation of chloroamination products such as 3-amino-4-chloromaleimides by a radical-type mechanism.
- An, Yu-Long,Zhang, He-Hui,Yang, Zhen-Hua,Lin, Long,Zhao, Sheng-Yin
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p. 5405 - 5414
(2016/11/22)
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- Preparation method of 3-amino-N-substituted maleimide compound
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The invention relates to a preparation method of a 3-amino-N-substituted maleimide compound. The preparation method is characterized in that the 3-amino-N-substituted maleimide compound has the structural formula shown in the description, in which R1 is phenyl or benzyl and NR2R3 is pyrrolidinyl, morpholinyl, benzylamino or dimethylamino. The preparation method comprises the following steps: adding N-substituted maleimide, an amine compound and a catalyst into a solvent, heating to 25-140 DEG C, enabling reaction for 1-12 hours and purifying to obtain the 3-amino-N-substituted maleimide compound. The 3-amino-N-substituted maleimide compound prepared by the preparation method provided by the invention is simple in reaction operation, relatively high in yield, short in reaction route, less in generation of waste gas, waste liquid and waste solid and easy to achieve industrial production.
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Paragraph 0023; 0057; 0058; 0060; 0062; 0064; 0066
(2018/02/04)
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- Synthesis of novel N-aryl-3-dialkylamino-4-substituted maleimides
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The syntheses of several novel 3-dialkylamino-N-aryl-maleimides 3a-i and 6 are described via a conjugate elimination addition-elimination pathway. Syntheses of their various 4-substituted derivatives 4a-i, 5a-c and 7-12 are also described. Introduction of a secondary amino group at C-3 position in N-arylmaleimides leads to the formation of enaminones 3a-i and 6, which undergo facile electrophilic substitutions at C-4 position in good to excellent yields to provide the highly functionalized maleimides 4a-i, 5a-c and 7-12.
- Patil, Nilesh S.,Deshmukh, Ganesh B.,Mahale, Keshao A.,Gosavi, Kirankumar S.,Patil, Sambhaji V.
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p. 272 - 278
(2015/03/04)
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- Vinyl Carbanions, 13. Convenient Synthesis of Oxaloacetic Acid Derivatives
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The vinyllithium derivatives 2a, b and 9a, b, obtained by direct lithiation of the functionally substituted acrylic acid derivatives 1a, b and 8a, b, respectively, react with heterocumulenes A - E such as phenyl isocyanate, phenyl isothiocyanate, and carb
- Schmidt, Richard R.,Talbiersky, Joerg,Betz, Rainer
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p. 2674 - 2678
(2007/10/02)
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