Einwirkung von Benzamidin auf einige aromatische Aldehyde

Kunckell, Franz; Bauer, Rebecca

doi:10.1002/cber.190103402270

Cited by 7 publications

(3 citation statements)

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“…From experiments with aliphatic and aromatic 1,2-diketones Pinner (109) concluded that the following reactions were general for these types of compounds: (81) reported that phenylglyoxal forms a condensation product with benzamidine. This product melted at nearly the same temperature as cyaphenine and may possibly be the latter (173).…”

Section: Nh-hclmentioning

confidence: 99%

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The Chemistry of the Amidines.

Shriner¹,

Neumann²

1944

Chem. Rev.

212

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Section: Nh-hclmentioning

confidence: 99%

“…of amidines with aldehydes Pinner (109,115,121) and Kunckell and Bauer(81) have shown that the following reaction of amidines is general:…”

mentioning

confidence: 99%

The Chemistry of the Amidines.

Shriner¹,

Neumann²

1944

Chem. Rev.

212

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“…The first 1,3-diaza-1,3-butadiene 3 was described by Pinner , in 1889 who synthesized it from benzamidine ( 1 ) and benzaldehyde ( 2 ) (Scheme ). An analogous product is obtained from salicylaldehyde, but nonaromatic aldehydes lead to different products . In 1907, Ley and Müller prepared the triphenyl compound 5 from N -phenylbenzimidoyl chloride 4 and benzamidine.…”

Section: Introductionmentioning

confidence: 99%

1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹

Guzmán¹,

Romero²,

Talamás³

et al. 1996

J. Org. Chem.

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Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4π + 2π] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on heating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the 1H-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by 1H NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes. These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.

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Ueber die Einwirkung von Mucobrom‐ und Mucochlor‐Säure auf Benzamidin

Kunckell

Zumbusch.

1902

Ber. Dtsch. Chem. Ges.

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Dieser Zusammenhang, den schon im Jahre 1865 der Entdecker des Serins in Erwagung gezogen hat '), iat urn so wahrscheinlicher , als faat alle natiirlich vorkommenden Aminosauren zur cc-Reihe gehoren.Auf Grund der Erkenntniss, dass Amido-und Sulfhydryl-Gruppe im Cystei'n aus C y s t i n s t e i n e n , im sogenannten t y p i s c h e n C y stei'n ( M o r n e r ) , an verschiedenen Kohlenstoffatomen haften, erhebt sich die Frage, oh auch das jiings? von 8;. A. H. M o r n e r und spater von E m d e n aus P r o t e i n s t o f f e n dargestellte C y s t e i ' n einen

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Einwirkung von Benzamidin auf einige aromatische Aldehyde

Cited by 7 publications

References 1 publication

The Chemistry of the Amidines.

The Chemistry of the Amidines.

1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹

Ueber die Einwirkung von Mucobrom‐ und Mucochlor‐Säure auf Benzamidin

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Einwirkung von Benzamidin auf einige aromatische Aldehyde

Cited by 7 publications

References 1 publication

The Chemistry of the Amidines.

The Chemistry of the Amidines.

1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines1

Ueber die Einwirkung von Mucobrom‐ und Mucochlor‐Säure auf Benzamidin

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1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹