Synthesis of Aminomethylglyoxal Derivatives

Balenović, K.; Bregant, N.

doi:10.1021/jo50010a008

Cited by 15 publications

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“…Removal of the phthalyl group by the method of Zng and Manske [48] yields aminopyruvaldehyde derivatives [49], which can be reduced very reidily with H2/Pt02 to rJ-amino-cr-hydroxypropaldehydes [50] and 3-aminopropane-l,2-diols [50,53]; with o-phenylenediamine, the pyruvaldehyde derivatives give arninoalkylquinoxalines, e.g. (39) [51].…”

Section: Alkmentioning

confidence: 99%

“…(39) [51]. The aminopyruvaldehyde derivatives can be converted into their diethylacetals or bis(ethy1enemercaptals) [49]. The corresponding acetals of phthalimido ethyl pyruvaldehyde wcre also prepared [50].…”

Section: Alkmentioning

confidence: 99%

“…The corresponding acetals of phthalimido ethyl pyruvaldehyde wcre also prepared [50]. The mild conditions in all steps of the synthesis make it possible to achieve complete retention of configuration at an asymmetric carbon atom, as in L-alanine or L-tyrosine [49,52].…”

Section: Alkmentioning

confidence: 99%

“…The nitrone [49], m.p. 153 "C, is formed in 50 % yield in the usual manner, as is the a-keto-aldehyde, (-)-cr-phthalimidomethyl pyruvaldehyde [49] ; the yield of aldehyde, based on the nitrone, is 80 %,, cci?…”

Section: Preparation Of ( -)-I -Bromo-3-phthalimido-2-butanonementioning

confidence: 99%

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Syntheses Using Pyridinium Salts (IV)

Kröhnke

1963

Angew. Chem. Int. Ed. Engl.

130

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Cleavage of N-phenylpyridinium or N-vinylpyridinium salts with secondary aliphatic amines leads to aromatic amino compounds or enamines which are often unobtainable by other routes. The other fragment, glutacondialdehyde or its rnonoanil, gives azulenes, as shown by Ziegler and Hafner, as well as Konig; these compounds can also be prepared from alkylpyridinium salts with cyclopentadienylsodium (Hafner). Syntheses of labile aldehydes which are otherwise dijjjcult to obtain and of a-ketocarboxylic acids, starting from pqiridinium salts and proceeding via nitrones or a-cyanoanils, are illustrated by many wcw examples. Benzimidazoles, benzothiazoles, and amidines are accessible from pyridinium salts via nitrones or a-cyanoanils; cyanoanils can be transformed into guinoxalines (including xanthopterine), perimidines, etc. Furthermore, nitrosonaphthols and nitrosonaphthylamines react with pyridinium salts containing an active iizethylene group on the nitrogq leading to new ring syslems. Further syn fhetic possihilities arise from nucleophilic &isplacements of the pyridine in pyriditiium salts by SN2 reactions. Combination of the route via nitrones with the methods of Arndt-Eistert, Ortoleva-King, or with chloromethylation constitutes a significant enlargement of its range of'application. The forniation of a-cyanoanils from diazoketones permits synthesis of a-keto-0-umino acids from a-amino acids, or of phenylglyoxylic acids from benzoic acids by chain extension.

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Section: Alkmentioning

confidence: 99%

Section: Alkmentioning

confidence: 99%

Section: Alkmentioning

confidence: 99%

Section: Preparation Of ( -)-I -Bromo-3-phthalimido-2-butanonementioning

confidence: 99%

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Syntheses Using Pyridinium Salts (IV)

Kröhnke

1963

Angew. Chem. Int. Ed. Engl.

130

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“…66°, [<*]d -34.7°± 1°( c, 0.14 in acetone). 1 Paper I, Balenovi6 and Bregant, J. Org. Chem., 17, 1328 (1952).…”

mentioning

confidence: 99%

Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of _L-alanine, β-alanine, and _L-tyrosine

Balenović¹,

Cerar²,

Filipović³

1953

J. Org. Chem.

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Derivatives of aminomethylglyoxal, the simplest of the series of aminoalkylglyoxals, have recently been prepared using glycine as starting material (1).We have now prepared, following the same method and starting with L-alanine, @-alanine, and L-tyrosine, the derivatives of the corresponding aminoalkylglyoxals (VIa-e).From the above mentioned amino acids, the N-phthaloylacyl chlorides (Ia-c), the diazoketones (Ha-c), and the bromoketones (IIIa-c) were prepared, from which, following the method of Krohnke and Bomer (2), the glyoxals (VIa-e) were obtained through the reaction stages IV-VI in the form of their N-phthaloyl derivatives.The bisethylenemercaptals and quinoxaline derivatives of these glyoxals were also prepared.a-Phthalimidoethylglyoxal (VIa) derived from L-alanine, and a-(phthalimid0)-@-(p-methoxypheny1)ethylglyoxal (VIc) derived from 0-methyl-L-tyrosine are optically active, showing [a], +8.7" and [a], -1.4" respectively.The N-phthaloylglyoxals (VIa-c) were obtained after filtration through a column of Alto3 and high vacuum distillation as yellow oils; the glyoxals of L-alanine and @-alanine ultimately crystallized.Aclcnmledgment, We are indebted to the Rockefeller Foundation for financial assistance. (IIIa). To a suspension of (-)-l-diazo-3phthalimidobutan-2-one (IIa, 5 9.) prepared following BalenoviO, Cerar, and Fuks (3) in glacial acetic acid (27.5 ml.), 48% hydrobromic acid (5.3 ml.) was added with stirring. After standing for an hour a t room temperature the reaction was complete. The mixture vim then diluted with 300 ml. of water and the crystals were collected. Yield, 6 g. (98.5%) of (-) -1-bro1no-3-phtha1imidobutan-2-one; recrystallization from ether-petroleum ether gave the pure compound, m.p. 66", [a]; -34.7' i 1" (c, 0.14 in acetone). EXPERIMENTAL All melting points are uncorrected. (-)-I -Bromo-3-phlhalimidobutan-2-one

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A

1997

Reaktionen Der Organischen Chemie

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Synthesis of Aminomethylglyoxal Derivatives

Cited by 15 publications

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Syntheses Using Pyridinium Salts (IV)

Syntheses Using Pyridinium Salts (IV)

Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of _L-alanine, β-alanine, and _L-tyrosine

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Synthesis of Aminomethylglyoxal Derivatives

Cited by 15 publications

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Syntheses Using Pyridinium Salts (IV)

Syntheses Using Pyridinium Salts (IV)

Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of L-alanine, β-alanine, and L-tyrosine

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Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of _L-alanine, β-alanine, and _L-tyrosine