Author Topic: Strecker Degradation References (Read 105 times)

no1uno · « **on:** September 09, 2009, 11:19:18 AM »

3 Here to start with - give people something they can search through and they won't "necessarily" have to ask

Synthesis of Indoleacetic Acid from Glutamic Acid and a Proposed Mechanism for the Conversion

Sidney W. Fox, Milon W. Bullock
J. Am. Chem. Soc., 1951, 73 (6), pp 2754–2755
DOI: 10.1021/ja01150a094

Quote

Abstract

An economical method for converting glutamic acid to indolacetic acid, through the intermediate succinaldehydic acid phenylhydrazone, has been developed. a-Ketoglutaric acid has been found as a byproduct in the preparation of the succinaldehydic acid. FOr the decomposition of the intermediate a-N-chloraminoglutaric acid there is a proposed mechanism which explains the formation of all the products from the reaction mixture.

Synthesis of Indole-3-acetic Acids and 2-Carboxyindole-3-acetic Acids with Substituents in the Benzene Ring

Sidney W. Fox, Milon W. Bullock
J. Am. Chem. Soc., 1951, 73 (6), pp 2756–2759
DOI: 10.1021/ja01150a095

Quote

Abstract

A number of indole-3-acetic acids are with substituents in the benzene ring have been prepared by the Fischer cyclization of the corresponding succinaldehydic acid phenylhydrazones which were in turn prepared by the sequence of reactions: glutamic acid --> succinaldehydic acid --> succinaldehydic phenylhydrazone. The 4- and 6- chloroindole-3-acetic acids have also been synthesized by condensation of the corresponding indolylmagnesium iodide complexes with chloroacetonitrile and subsequent hydrolysis of the nitriles to the acids. Several of the corresponding substituted 2-carboxyindole-3-acetic acids have been obtained by the cyclization of the substituted a-ketoglutaric acid phenylhydrazones resulting either as byproducts from the preparation of the succinaldehydic acid phenylhydrazones or, in the form of their diethyl esters, by the Japp-Klingemann reaction between ethyl a-acetoglutarate and a phenyldiazonium salt.

The Strecker Degradation of ?-Amino Acids.

Alexander. Schonberg, Radwan. Moubacher
Chem. Rev., 1952, 50 (2), pp 261–277
DOI: 10.1021/cr60156a002

(No abstract for the big one)

THANKS

java · « **Reply #1 on:** September 09, 2009, 12:07:41 PM »

Synthesis of Indoleacetic Acid from Glutamic Acid and a Proposed Mechanism for the Conversion
Sidney W. Fox, Milon W. Bullock
J. Am. Chem. Soc.,1951, 73 (6), pp 2754–2755

Abstract
An economical method for converting glutamic acid to indolacetic acid, through the intermediate succinaldehydic acid phenylhydrazone, has been developed. a-Ketoglutaric acid has been found as a byproduct in the preparation of the succinaldehydic acid. FOr the decomposition of the intermediate a-N-chloraminoglutaric acid there is a proposed mechanism which explains the formation of all the products from the reaction mixture.

java · « **Reply #2 on:** September 09, 2009, 12:13:15 PM »

Synthesis of Indole-3-acetic Acids and 2-Carboxyindole-3-acetic Acids with Substituents in the Benzene Ring
Sidney W. Fox, Milon W. Bullock
J. Am. Chem. Soc. 1951, 73 (6), pp 2756–2759

Abstract
A number of indole-3-acetic acids are with substituents in the benzene ring have been prepared by the Fischer cyclization of the corresponding succinaldehydic acid phenylhydrazones which were in turn prepared by the sequence of reactions: glutamic acid --> succinaldehydic acid --> succinaldehydic phenylhydrazone. The 4- and 6- chloroindole-3-acetic acids have also been synthesized by condensation of the corresponding indolylmagnesium iodide complexes with chloroacetonitrile and subsequent hydrolysis of the nitriles to the acids. Several of the corresponding substituted 2-carboxyindole-3-acetic acids have been obtained by the cyclization of the substituted a-ketoglutaric acid phenylhydrazones resulting either as byproducts from the preparation of the succinaldehydic acid phenylhydrazones or, in the form of their diethyl esters, by the Japp-Klingemann reaction between ethyl a-acetoglutarate and a phenyldiazonium salt.

java · « **Reply #3 on:** September 09, 2009, 12:18:22 PM »

The Strecker Degradation of ?-Amino Acids.
Alexander. Schonberg, Radwan. Moubacher
Chem. Rev.,1952, 50 (2), pp 261–277

I. Introduction.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 261
y inorganic agents . , . . , . . , , . 262
111. Strecker degradations effected by organic agents..
A. Degradations effected by ketones and aldehydes.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
1. Degradations effected by ketones.. . . . . . . . . . , , . 263
2. Degradations effected by nitrogen analogs of 0- and p-quinones.. . . . . . . . . . 266
3. Degradation of amino acids by the action of isatin in the pr
or methylene blue.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4. Degradations effected in the presence of a base . . . . . . . . . . .
5. Degradations effected by aldehydes. . . . . . . . . . . . . . . . . . . . . . . . . . . .
6. Biochemically important aldehydes and ketones as degrad
7 . Reaction mechanism of degradation by carbonyl compounds.. . . . . . . . . . . . . 268
8. Final fate of the amino group in Strecker degradations.. . . . . . . . . . . . . . . . . . 270
9. Utilization of the degrading power of ketones in the elucidation of structure. 270
ketones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271
11. Strecker degradatio
10. Quantitative methods based on Strecker degradations effected by poly-
B. Reactions allied to the Strecker degradation effected by keto
1. Conversion of benzylamine to benzaldehyde. . . . . . . . . . . . . . .
2. Transamination reactions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3. Action of methylglyoxal and peri-naphthindantrione on aspartic acid.. . . . . . 272
4. Nature of the color accompanying the degradation of amino acids by ninhydrin
and pcri-naphthindantrione hydrate.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 272
5. The phenanthraquinonimine test for compounds containing the group
>cH?*“*. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 273
C. Degradations effected by miscellaneous compounds., . . . . . . . . . . . . . . . .
IV. Strecker degradations effected in the presence of a catalyst.. . . . . . . . .
A. Degradations effected in the presence of a catalyst and oxygen.. .
B. Degradations effected in the absence of oxygen ...................
V. References. . . . . . ............................................... 276

no1uno · « **Reply #4 on:** November 05, 2009, 07:24:13 AM »

I'll add these onto this thread - I have a bunch more online - when I have the time, I'll grab 'em and throw 'em up here as well, so there is one thread

Author Topic: Strecker Degradation References (Read 105 times)

no1uno

Strecker Degradation References

java

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java

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java

Re: Strecker Degradation References

no1uno

Re: Strecker Degradation References