- Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes
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A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.
- Wippert, Nicolai A.,Jung, Nicole,Br?se, Stefan
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supporting information
p. 568 - 572
(2019/09/03)
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- A General and Direct Reductive Amination of Aldehydes and Ketones with Electron-Deficient Anilines
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In our ongoing efforts in preparing tool compounds for investigating and controlling the biosynthesis of phenazines, we recognized the limitations of existing protocols for C-N bond formation of electron-deficient anilines when using reductive amination. After extensive optimization, we have established three robust and scalable protocols for the reductive amination of ketones with electron-deficient anilines, by using either BH3·THF/AcOH/CH2Cl2 (method A), with reaction times of several hours, or the more powerful combinations BH3·THF/TMSCl/DMF (method B) and NaBH4/TMSCl/DMF (method C), which give full conversions for most substrates within 10 to 25 minutes. The scope and limitations of these reactions have been defined for 12 anilines and 14 ketones.
- Pletz, Jakob,Berg, Bernhard,Breinbauer, Rolf
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p. 1301 - 1317
(2016/05/02)
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- Oxidative Cleavage of C2-C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates
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On reaction with (diacetoxyiodo)benzene, isatin and N-acetyl isatin undergo the oxidative C2-C3 bond cleavage to form carbamates of alkyl anthranilates and alkyl 2-acetamidobenzoate, respectively.
- Kalbandhe, Amit H.,Kavale, Ashish C.,Thorat, Prerana B.,Karade, Nandkishor N.
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supporting information
p. 763 - 768
(2016/03/12)
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- Study of alkaloids of the Siberian and Altai flora 12. Synthesis of new lappaconitine derivatives containing olefinic substituents
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Lappaconitine and N-deacetyllappaconitine derivatives containing bromine and iodine atoms in the aromatic moiety were synthesized. The Heck cross-coupling of these halides with ethyl acrylate or 2-methyl-5-vinylpyridine afforded new olefinated lappaconitine derivatives.
- Osadchii,Shul'ts,Polukhina,Shakirov,Tolstikov
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p. 1077 - 1084
(2008/02/01)
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- Oxidative Bromination of Aromatic Amides using Sodium Perborate as Oxidant
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Sodium perborate in glacial acetic acid-acetic anhydride with potassium bromide and sodium tungstate as a catalyst, provides a novel system for the bromination of aromatic amides.
- Hanson, James R.,Harpel, Simone,Medina, Inmaculada C. Rodriguez,Rose, Dorian
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p. 432 - 433
(2007/10/03)
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- Catalysts for the Oxidative Bromination of Aromatic Amines and their N-Acetyl Derivatives
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In the nuclear bromination of aromatic amines by bromide and hydrogen peroxide in acetic acid, sodium tungstate has been compared with ammonium molybdate and ammonium vanadate, and found to be an effective catalyst.
- Hanson, James R.,Opakunle, Alexander,Petit, Philippe
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- Process for the preparation of 2-chloro and 2,6-dichloroanilines
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2-Chloro and 2,6-dichloroanilines, optionally substituted in the 3-, 5-, and/or 6-position are prepared from the corresponding anilides by selective bromination, chlorination, reduction and hydrolysis. The selectivity of the process for introducing chlorines ortho to the amino group is very high.
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