- One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine
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Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).
- Golub, Tatiana,Dou, Gui-Yuan,Zeng, Cheng-Chu,Becker, James Y.
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supporting information
p. 7961 - 7964
(2019/10/11)
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- Selectfluor-mediated oxidative methylenation of amide with N, N -dimethylpropanamide for N, N ′-methylenebisamide synthesis
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A simple and efficient approach for the synthesis of N,N′-methylenebisamides through a Selectfluor-mediated oxidative reaction of aromatic amides and N,N-dimethylpropanamide (DMP) is described. Remarkable results clearly reveal that DMP plays a dual role in this reaction, as both a one-carbon source and an environment-friendly solvent. Moreover, the process provides new strategies for the synthesis of bisamides with advantages of operationally simple, insensitive to atmospheric conditions, and good to high yields.
- Cao, Yue,Zhou, Dongheng,Ma, Yongmin
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- Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications
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Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general and efficient access to symmetrical methylenebisamides from primary amides. This methodology was used to achieve a three-component Mannich reaction using acetophenone, saccharin and DMSO to furnish a β-amino ketone. It also provided a metal-free synthesis of thiadiazole and bis(phenyl)methane. Effectively, this method uses DMSO as a safer surrogate to formaldehyde. A mechanism for methylenebisamide formation involving radical intermediates has been proposed based on mechanistic studies.
- Mahajan, Pankaj S.,Tanpure, Subhash D.,More, Namita A.,Gajbhiye, Jayant M.,Mhaske, Santosh B.
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p. 101641 - 101646
(2015/12/08)
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- A convenient and clean synthesis of methylenebisamides and carbinolamides over zeolites in aqueous media
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A simple, efficient and environmentally benign protocol for the synthesis of methylenebisamides and carbinolamides in high yields from aromatic amides and formaldehyde in the presence of heterogeneous catalysts (Hβ and NaY zeolites) using water as a solvent is demonstrated. Moreover, the catalyst is recyclable and can be reused without significant loss in its catalytic activity.
- Mameda, Naresh,Marri, Mahender Reddy,Peraka, Swamy,Macharla, Arun Kumar,Kodumuri, Srujana,Chevella, Durgaiah,Naresh, Gutta,Nama, Narender
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- Synthesis of methylenebisamides by TFA-promoted reactions of nitriles and DMSO
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Under TFA promoted conditions, aryl and 2-pyridyl nitriles can react with DMSO, affording methylenebisamides in moderate to good yields. While the electron-donating groups give good yields, the electron-withdrawing groups provide lower yields.
- Pan, Lingxia,Huang, Lin,Xie, Chunsong
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p. 770 - 773
(2014/03/21)
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- Reactions of Trimethylsilylmethyl Azide with Aromatic Acid Derivatives Catalyzed by Fluoride Ion
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The treatment of an aromatic acid halide with trimethylsilylmethyl azide (TMSMA) in the presence of potassium fluoride and crown ether gave triazine, methanediamine, and benzamide derivatives, while the reaction of acid anhydride with TMSMA gave tertiary amine together with methanediamine and benzamide under similar conditions.
- Nishiyama, Kozaburo,Mikuni, Hioruki,Harada, Mari
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p. 3381 - 3382
(2007/10/02)
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