Conversion of α‐Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid

@article{Hiegel2004ConversionO,
  title={Conversion of $\alpha$‐Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid},
  author={Gene A. Hiegel and Justin C. Lewis and Jason W. Bae},
  journal={Synthetic Communications},
  year={2004},
  volume={34},
  pages={3449 - 3453}
}
Abstract Trichloroisocyanuric acid oxidation of α‐amino acids in water or methanol in the presence of pyridine produces nitriles with one less carbon in good yields and of high purity. 
View on Taylor & Francis
the-hive.archive.erowid.org
15 Citations

15 Citations

Citation Type

Citation Type

Biobased synthesis of acrylonitrile from glutamic acid
Glutamic acid was transformed into acrylonitrile in a two step procedure involving an oxidative decarboxylation in water to 3-cyanopropanoic acid followed by a decarbonylation-elimination reaction… Expand
Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids.
TLDR
This heterogeneous catalytic system was applied successfully to convert a protein-rich byproduct from the starch industry into useful bio-based N-containing chemicals. Expand
Trichloroisocynuric Acid/DMF as Efficient Reagent for Chlorodehydration of Alcohols Under Conventional and Ultrasonic Conditions
A new and efficient method for the chlorodehydration of alcohols utilizing TCCA/DMF is described. Various alcohols can be converted smoothly into their corresponding alkyl chlorides in high yields… Expand
A one-pot oxidative decarboxylation-Friedel-Crafts reaction of acyclic alpha-amino acid derivatives activated by the combination of iodobenzene diacetate/iodine and iron dust.
An efficient one-pot oxidative decarboxylation-Friedel-Crafts reaction of acyclic alpha-amino acid derivatives with electron-rich aromatic compounds is reported. The reaction is activated by the… Expand
Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources
In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers… Expand
Electrochemical Routes for the Valorization of Biomass-Derived Feedstocks: From Chemistry to Application
The drive to reduce consumption of fossil resources, coupled with expanding capacity for renewable electricity, invites the exploration of new routes to utilize this energy for the sustainable prod...
Controlled defunctionalisation of biobased organic acids.
TLDR
This feature article intends to highlight the recent progress in heterogeneous chemocatalytic defunctionalisation of the widely available citric and amino acids, focusing on the different chemical routes available and identifying the most promising defunctionsalisation strategies based on atom economy and functionality index. Expand
Synthesis of stable isotope-labeled nasturlexins and potential precursors to probe biosynthetic pathways of cruciferous phytoalexins.
  • M. Pedras, Q. H. To
  • Chemistry, Medicine
  • Journal of labelled compounds & radiopharmaceuticals
  • 2018
TLDR
Application of an efficient deuterium-hydrogen exchange transformation to nonlabeled starting materials allowed access to new deuterated compounds, including 3-hydroxyphenylethyl glucosinolate. Expand
Protein-Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities.
TLDR
This Review describes every process step in the value chain from protein waste to chemicals, and physical and (bio)chemical technologies for the production of polymers, commodity chemicals, pharmaceuticals, and other fine chemicals are described. Expand
Application of N-halo reagents in organic synthesis
This review article summarizes published data on the application of N-halo reagents (such as N-halo amines, N-halo amides and/or imides, N-halo sulfonamides and/or imides, and etc.) in various… Expand
...
1
2
...

References

SHOWING 1-7 OF 7 REFERENCES
One-step transformation of α-amino acids to α-amino aldehydes effected by electrochemical oxidation of Ph3P
Abstract The electrolysis of triphenylphosphine and L-α-amino acids in one compartment cell under a nitrogen atmosphere at −30°C gave L-α-amino aldehydes in good yields with no or little racemization… Expand
Oxidation by persulphate. Part V. Silver-catalysed oxidation of secondary aliphatic amines and α-amino-acids
Silver-catalysed oxidation by cold aqueous persulphate, which converts primary aliphatic amines into aldehydes or ketones, gave poorer yields when applied to related secondary amines of the types… Expand
SYNTHESIS OF OPTICALLY ACTIVE ALIPHATIC NITRILES FROM ALDEHYDES AND ACIDS
Abstract Optically active nitriles are very useful starting products for the preparation of chiral amines1, ketones2 and pyridines3. They are usually accessible from the corresponding acids via amide… Expand
Products at the reaction of amino acids in aqueous solution with chlorine
24種類のアミノ酸と塩素との水溶液中における反応生成物を各フラクションに分けて, GCおよびGC/MSを用いて同定を行った。揮発性有機塩素化合物として, 多くのアミノ酸からクロロホルム, 四塩化炭素, トリクロロエチレン, クロロピクリンが検出された。ペンタン抽出物質として, 各アミノ酸の炭素数が1個少ないアルデヒドおよびニトリルが検出された。またフェニルアラニンの場合,… Expand
The Sadtler handbook of infrared spectra
Argentic oxide oxidations of organic compounds
Orthoesters and Related Compounds from Malono- and Succinonitriles