PREPARATION OF SEVERAL SUBSTITUTED HYDANTOINS<sup>1</sup>

Thompson, T. J.; Bedell, Harold L.; Buffett, George M.

doi:10.1021/ja01680a042

Cited by 7 publications

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“…The synthesis of hydantoins through the action of alkali hypohalites on disubstituted cyanoacetamides has found wide application in the preparation of 5,5-disubstituted hydantoins (123,127,136,139,140,141,217,218,219,220,324,326,445,573,598). This reaction was first studied by Errera (213), who reported that this synthesis is not applicable to unsubstituted hydantoin.…”

Section: N Cyanoacetamides and Alkali Hypohalitesmentioning

confidence: 99%

The Chemistry of the Hydantoins.

Ware¹

1950

Chem. Rev.

450

203

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Section: N Cyanoacetamides and Alkali Hypohalitesmentioning

confidence: 99%

The Chemistry of the Hydantoins.

Ware¹

1950

Chem. Rev.

450

203

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Urech Hydantoin Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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The formation of hydantoins by means of the treatment of α‐amino acids with potassium cyanate in aqueous solution and is generally referred to as the Urech hydantoin synthesis. This reaction is a two‐step process. The study finds that the α‐amino acid is water soluble, whereas hydantoins are only slightly soluble in water. This reaction has been used to separate amino acids after the hydrolysis of protein; the resulting hydantoins are then converted into the α‐amino acids. This reaction has been modified by the reaction of potassium cyanate with α‐amino nitriles in glacial acetic acid. This reaction has been applied for the preparation of hydantoins.

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Δ‐Pyrroline aus Alkinyl‐hydantoinen

Schulte

Reisch

Plener

1970

Archiv der Pharmazie

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a-Amino-hexin-(5)-carbonsiiuren (11) lassen sich nicht durch alkalische bzw. saure Hydrolyse BUS 5-Butinyl-hydantoinen (I) darstellen. Nach kiirzerer Einwirkungszeit (2l/* bis 5 SM.) von 15proz. HCl erfolgt Wasseranlagerung an die Dreifachbindung, es entstehen Oxoalkyl-hydantoine (IV). Mit stiirkcrer SalzsLure (25 yo) und liingerer Einwirkung entstehen Pyrrolin-carbons%uren (111). Letztere treten auch dann auf, wenn die Butinylhydantoine mit Bargtlauge bei 150' (15 atii) verseift werden. Propinyl-cycloalkampirohydantoine (VII) verhalten sich bei smrer Hydrolyse gleich; es bilden sich Cycloalkanopyrrolin-carbons%uren (IX) . d l-Pyrrohes from AUdnyl-hydantoins a-Amino-5-heme carboxylic acids (11) cannot be synthesized from 5-butynyl-hydmtoins by alkaliue or acidic hydrolysis. After a shorter reaction time (211a to 5 hours) with approximately 15% hydrochloric acid, addition of wicter to the triple bond takes place resulting in oxoalkyl-hydantoins (IV). Pyrroline carboxylic acids (111) are formed under the action of stronger hydrochloric acid (about 25%) during a longer reaction time. These reaction products are also obtained if the butynyl-hydantoins are saponified by barium hydroxide at 150' C (220 p. s. i.). F'ropynyl-cycloalkyl-spiro-hydantoh (VII) show the same behaviour towards acidic hydrolysis; cycloalkyl-p.pline carboqlic acids (IX) are formed.Es konnte friiher gezeigt werdenl), dafl sich 1-Propinylbarbitursiiuren dann zu Oxazolinyluracilen cyclisieren lassen, wenn sie am C-5 monosubstituiert sind. Dagegen gehen 3bzw. 5-Propinyl-hydantoine analoge Ringschluflreaktionen nicht einl). 5-Alkyl-(bzw. Aryl)-5-butinyl-hydantoine (I), die nach Bucherer2) und Bergs3) in guten Ausbeuten aus Alkinonen erhalten werden, sollten sich zu a-Amino-alkincarbonsauren (11), die in jiingster Zeit in Pflanzen aufgefunden wurden4), verseifen lassen.Bei der alkalisohen Hydrolyse mit Ba( OH), bei 100" trat keine Veriinderung der Ausgangssubstanz ein. Erst beim Erhitzen auf 150' bei 15 atus) entatanden neue

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PREPARATION OF SEVERAL SUBSTITUTED HYDANTOINS¹

Cited by 7 publications

References 0 publications

The Chemistry of the Hydantoins.

The Chemistry of the Hydantoins.

Urech Hydantoin Synthesis

Δ‐Pyrroline aus Alkinyl‐hydantoinen

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PREPARATION OF SEVERAL SUBSTITUTED HYDANTOINS1

Cited by 7 publications

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The Chemistry of the Hydantoins.

The Chemistry of the Hydantoins.

Urech Hydantoin Synthesis

Δ‐Pyrroline aus Alkinyl‐hydantoinen

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PREPARATION OF SEVERAL SUBSTITUTED HYDANTOINS¹