141:
66:
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Alan D. Borthwick. 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal
Chemistry, and Bioactive Natural Products. DrugMolDesign, 15 Temple Grove, London NW11 7UA, U.K. Chem. Rev., 2012, 112 (7), pp 3641–3716. DOI:
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263:
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Cara E. Humphrey, Markus
Furegati, Kurt Laumen, Luigi La Vecchia, Thomas Leutert, J. Constanze D. Müller-Hartwieg, and Markus Vögtle (2007). "Optimized Synthesis of
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can be used as a methylene component as well; its condensation products with aromatic aldehydes, on reduction and hydrolysis give the corresponding amino acids.
140:
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H.D. Dakin. Aromatic aldehyde derivatives of proteins, peptides and amino acids. J. Biol. Chem. 1929, 84:675-682
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to the azlactone (not displayed) which is ring-opened with sodium acetate in methanol to dehydroamino acid
212:
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Variants of the azlactone synthesis in which analogues of azlactones are used are sometimes advantageous.
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215:[On the condensation of hippuric acid with phthalic acid anhydride and with benzaldehyde].
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113:
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A. M. Asiri. New
Conjugated Systems Derived from Piperazine-2,5-dione. Molecules 2000, 5, 629-636
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Organic
Syntheses Based on Name Reactions: A Practical Guide to 750 Transformations
213:"Ueber die Condensation der Hippursäure mit Phtalsäureanhydrid und mit Benzaldehyd"
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have each been employed as the enolate-forming component of the condensation.
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In one study the
Erlenmeyer amino acid synthesis was used in the heart of an
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which is able to only cleave the methyl ester of the S-enantiomer (forming (
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G. E. VandenBerg, J. B. Harrison, H. E. Carter, B. J. Magerlein (1973).
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181:[On some derivatives of benzoyl-imido-cinnaminic acid].
88:. This intermediate also has two acidic protons and reacts with
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485:(the benzyl ether group is also cleaved). This compound is
92:, acetic anhydride and sodium acetate to a so-called
29:
Erlenmeyer–Plöchl azlactone and amino acid synthesis
80:derivative of glycine, cyclizes in the presence of
35:who partly discovered the reaction, is a series of
69:Azlactone chemistry: step 2 is a Perkin variation
517:untouched. The final step is amide cleavage to (
179:"Über einige Derivate der Benzoylimidozimtsäure"
184:Berichte der deutschen chemischen Gesellschaft
346:(3rd ed.). CRC Press. pp. 219–220.
96:. This compound on reduction gives access to
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429:: CS1 maint: multiple names: authors list (
340:Richard O.C. Norman, James M. Coxon (1993).
262:: CS1 maint: multiple names: authors list (
403:-Tyrosine Suitable for Chemical Scale-Up".
313:Alfred Hassner, Irishi Namboothiri (2011).
405:Organic Process Research & Development
481:gives the N-acyl-m-tyrosine methyl ester
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285:H. B. Gillespie, H. R. Snyder (1934).
255:
201: ; see especially pp. 1623-1624.
33:Friedrich Gustav Carl Emil Erlenmeyer
7:
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564:Chemical synthesis of amino acids
139:
343:Principles of Organic Synthesis
233: ; see especially pp. 3-8.
84:, condensing to give 2-phenyl-
1:
554:Heterocycle forming reactions
112:(in Bergmann modification),
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301:, vol. 2, p. 489
273:, vol. 5, p. 946
509:) leaving water-soluble (
454:reacts with the N-acetyl
319:. Elsevier. p. 139.
229:10.1002/jlac.18932750102
197:10.1002/cber.18840170215
493:is brought about by an
211:Erlenmeyer, F. (1893).
549:Condensation reactions
245:"2-Phenyl-2-oxazolone"
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449:3-hydroxybenzaldehyde
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287:"dl-β-Phenylalanine"
122:2,5-Diketopiperazine
177:Plöchl, J. (1884).
153:Dakin-West reaction
39:which transform an
18:Azlactone synthesis
491:kinetic resolution
217:Annalen der Chemie
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58:(also known as an
37:chemical reactions
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417:10.1021/op700093y
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376:10.1021/cr200398y
299:Collected Volumes
292:Organic Syntheses
271:Collected Volumes
250:Organic Syntheses
50:to various other
16:(Redirected from
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467:acetic anhydride
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479:Hydrogenation
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114:thiohydantoin
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98:phenylalanine
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74:Hippuric acid
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258:cite journal
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134:L-m-tyrosine
131:
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90:benzaldehyde
72:
40:
28:
26:
505:soluble in
136:synthesis
52:amino acids
543:Categories
529:-tyrosine
164:References
104:Variations
118:rhodanine
110:Hydantoin
94:azlactone
86:oxazolone
78:benzamide
60:azlactone
56:oxazolone
147:See also
487:racemic
460:glycine
223:: 1–8.
54:via an
48:glycine
495:enzyme
350:
323:
76:, the
456:amide
128:Scope
489:and
469:and
443:The
431:link
348:ISBN
321:ISBN
264:link
116:and
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Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
