- KOtBu-Mediated Reductive Cyanation of Tertiary Amides for Synthesis of α-Aminonitriles
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A simple, mild, catalyst-free, and efficacious KOtBu-mediated reductive cyanation reaction of tertiary amides under hydrosilylation conditions has been described. A series of α-aminonitriles is obtained in moderate to high yield with good functional group tolerance. The reaction works well with a readily available amide substrate, a cheap and versatile base KOtBu, and a commercially available hydrosilane (EtO)3SiH and is convenient for workup and purification.
- Liu, Liwen,Liu, Yu,Shen, Xue,Zhang, Xiao,Deng, Shengqi,Chen, Yang
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p. 6321 - 6329
(2022/04/22)
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- Strecker reactions with hexacyanoferrates as non-toxic cyanide sources
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The Strecker reaction is the most widely applied three-component reaction. Although highly useful for the preparation of α-amino nitriles, α-amino acids, hydantoins and numerous related compounds, the need for the application of toxic sources of HCN limits its application in both academic and industrial settings. Here, we present a facile protocol for Strecker reactions using a mixture of potassium ferri- and ferrocyanides as a non-toxic substitute.
- Grundke, Caroline,Opatz, Till
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supporting information
p. 2362 - 2366
(2019/05/17)
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- 1-Cyanoformamidines. Formation during the RuO4-mediated oxidation of secondary amines
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When performed in the presence of cyanide and at pH smaller than 5, the RuO4-mediated oxidation of secondary amines Bn-NH-R (1a-b; R=Me, Et) gave mainly 1-cyanoformamidines Bn-NR-C(=NH)-CN (2a-b) and their hydrolysis products Bn-NR-COCN (3a-b), Bn-NR-CN (4a-b), Bn-NR-CONH2 (5a-b). Carboxamides 5a-b can result also directly from 1a-b. (Chemical Equation Presented).
- Florea, Cristina,Stavarache, Cristina,Petride, Horia
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p. 319 - 325
(2016/10/11)
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- RuO4-mediated oxidation of secondary amines. Part 1. Are hydroxylamines the main intermediates?
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The RuO4-catalyzed oxidation of secondary amines Bn-NH-CH2R (1a and b; R=H, Me) gave mainly amides, but minute amounts of nitrones PhCH=N(O)-CH2R (9a and b) and traces of Bn-N(OH)-CH2R (R=H, 4a) were also detect
- Florea, Cristina A.,Petride, Horia
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p. 475 - 486
(2016/07/20)
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- Redox-neutral α-cyanation of amines
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α-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine α-cyanation/N-alkylation or alternatively, α-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.
- Ma, Longle,Chen, Weijie,Seidel, Daniel
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p. 15305 - 15308
(2012/10/29)
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- The decarboxylative strecker reaction
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α-Amino acids react with aldehydes in the presence of a cyanide source to form α-amino nitriles in what can be considered a decarboxylative variant of the classical Strecker reaction. This unprecedented transformation does not require the use of a metal catalyst and provides facile access to valuable α-amino nitriles that are inaccessible by traditional Strecker chemistry.
- Das, Deepankar,Richers, Matthew T.,Ma, Longle,Seidel, Daniel
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supporting information; experimental part
p. 6584 - 6587
(2012/01/19)
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- Solvent-free synthesis of racemic α-aminonitriles
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A very simple one-step, environmentally friendly procedure for the synthesis of α-aminonitriles from aldehydes and ketones, using trimethylsilyl cyanide in the absence of solvent, is reported. The active catalyst of this three-component (Strecker) reaction was the amine employed in the transformation. In general, aldehydes react more rapidly than ketones and give almost quantitative yields of the corresponding α-aminonitriles in less than fifteen minutes. However, only cyclic ketones afford the corresponding α-aminonitriles in excellent chemical yields under these conditions. Georg Thieme Verlag Stuttgart.
- Baeza, Alejandro,Najera, Carmen,Sansano, Jose M.
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p. 1230 - 1234
(2008/02/02)
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- La(O-i-Pr)3 catalyzed three-component condensation reaction: A convenient synthesis of N,N-dialkyl-α-cyanoamines
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In the presence of 10 mol% of La(O-i-Pr)3, a three-component condensation reaction of aldehyde, secondary amine and trimethylsilylcyanide proceeded smoothly to afford N,N-dialkyl-α-cyanoamine in good yield.
- Sun, Peipei,Qian, Changtao,Wang, Limin,Chen, Ruifang
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p. 2973 - 2978
(2007/10/03)
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- A novel oxidative transformation of α-aminonitriles to amides
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A novel oxidative transformation of α-aminonitriles to amides is reported. Oxidation of α-aminonitriles with peracid, followed by basic treatment affords, amides in good yields. A mechanistic aspect of this transformation is also discussed.
- Yokoshima, Satoshi,Kubo, Tetsuji,Tokuyama, Hidetoshi,Fukuyama, Tohru
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p. 122 - 123
(2007/10/03)
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