- Traceless selenocarboxylates for the one-pot synthesis of amides and derivatives
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We have recently reported a one-pot procedure for glycosyl amides synthesis using selenocarboxylate as traceless reagent. Herein, we present a further application of selenocarboxylate-azide reaction for amide bond formation on a broader range of substrates, including heterocyclic systems and fatty acid. This method proved to be highly efficient for the synthesis of primary and secondary amides, sulfonamides, imides, phosphoramide and also carbamate.
- Silva, Luana,Rosário, Alisson R.,Machado, Bianca M.,Lüdtke, Diogo S.
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supporting information
(2020/12/25)
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- Vanadium-Catalyzed Oxidative C(CO)-C(CO) Bond Cleavage for C-N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides
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A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N′-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.
- Digwal, Chander Singh,Yadav, Upasana,Ramya, P. V. Sri,Sana, Sravani,Swain, Baijayantimala,Kamal, Ahmed
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p. 7332 - 7345
(2017/07/26)
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- Copper-catalyzed synthesis of imides from aldehydes or alcohols and amine hydrochloride salts
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An efficient approach to imides has been developed. With tert-butyl hydroperoxide (TBHP) as the oxidant, CuBr (20 mol-%) as the catalyst, and PhI(OAc)2 (50 mol-%) as the additive, aldehydes or alcohols reacted with amine hydrochloride salts to provide imides in moderate to good yields. A possible reaction pathway for the formation of the products is also discussed in this paper.
- Yu, Hui,Zhang, Yonghao
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p. 1824 - 1828
(2015/05/27)
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- TBHP/TEMPO-mediated oxidative synthesis of imides from amides
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A new protocol for the synthesis of imides has been developed. In the presence of copper catalyst, N-benzylamides were oxidized to the corresponding imides by TBHP/TEMPO system in moderate to good yields. Imides were synthesized through the oxidation of N-benzylamides by TBHP/TEMPO system in moderate to good yields.
- Yu, Hui,Chen, Yuegang,Zhang, Yonghao
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p. 531 - 534
(2015/05/27)
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- Palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines
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A novel and efficient palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of a variety of valuable imides and tertiary benzanilides under an atmospheric pressure of CO. Copyright
- Ran, Longfei,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 577 - 583
(2014/02/14)
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- Novel chromium(VI) catalyzed oxidation of N-alkylamides to imides with periodic acid
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A novel and practical procedure for preparation of imides is described using chromium(VI) oxide to catalyze the oxidation of N-alkylamides with periodic acid in the presence of acetic anhydride in acetonitrile.
- Xu, Liang,Zhang, Suhong,Trudell, Mark L.
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p. 1668 - 1669
(2007/10/03)
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- Efficient Preparations of Acylamides, Acylcarbamates and Acylureas from Alk-1-en-2-yl Esters
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Acylamides, acylcarbamates and acylureas have been synthesized by acylation of amides, carbamates and ureas sodium salts with alk-1-en-2-yl esters prepared with 2 as catalyst.
- Seiller, Benedicte,Heins, Dorothee,Bruneau, Christian,Dixneuf, Pierre H.
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p. 10901 - 10912
(2007/10/02)
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- Incorporation of molecular nitrogen into organic compounds III. Reaction of titanium-nitrogen complexes with acid halides and acid anhydrides
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The titanium-nitrogen complex 1, prepared from TiCl3 or TiCl4 and Mg in THF under nitrogen reacts with acid chloride to give amide and/or imide.The cyclic imides were obtained by the reaction of titanium-isocyanate complex 3, , made from titanium-nitrogen complex 1 and carbon dioxide, and the corresponding cyclic acid anhydrides.Benzoxazone derivatives afforded the corresponding quinazoline derivatives in a similar procedure.These results indicate that molecular nitrogen was incorporated into organic compounds via titanium nitrogen complexes.
- Mori, Miwako,Uozumi, Yasuhiro,Shibasaki, Masakatsu
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p. 255 - 267
(2007/10/02)
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- PHOTOCHEMICAL AND THERMAL REACTIONS OF HETEROCYCLES. IV. PHOTO-OXIDATION REACTIONS OF MESOIONIC DITHIOLIUMOLATE, THIAZOLIUMOLATE, AND RELATED HETEROCYCLES. SOLVENT EFFECTS ON THE COURSE OF THE PHOTO-OXIDATION
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Photo-oxidation of mesoionic 1,3-dithiolium-4-olates (1) gave diacyl disulfide (2), and that of a mesoionic thiazolium-4-olate (6) and oxazolium-5-olate (9) gave diacylamides as the main products.The formation of these products was rationalized by a route involving fragmentation of the corresponding endoperoxides, which are formed by cycloaddition of singlet oxygen on the mesoionic rings.Photo-oxidation of 5(4H)-oxazolones (12) and a 5(4H)-thiazolone (17) in dichloromethane gave the corresponding dehydro-dimers, while that of the former in dimethylformamide gave mainly diacylamides.The acylamides were considered to arise via the endoperoxides of the mesoionic tautomers.
- Kato, Hiroshi,Tani, Kazue,Kurumisawa, Haruki,Tamura, Yoshiko
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p. 1313 - 1322
(2007/10/02)
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