Reaktionen von Arylidentetralonen mit Cyanessigs�urederivaten

Otto, Hans‐Hartwig; Schmelz, Herbert

doi:10.1007/bf00911912

Cited by 11 publications

(2 citation statements)

References 2 publications

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“…Attempts were made to prepare 2-methylpyrimidone derivative E by cyclization of the 3-aminophenanthrene derivatives 1 , 2 , 4 and 5 with acetic anhydride either in the presence or the absence of conc. H 2 SO 4 adopting the same procedure reported in the literature [37,38,39,40], but these reactions afforded the N , N -diacetylaminophenanthrenes 10 – 13 instead of the expected pyrimidone derivatives (Scheme 4).…”

Section: Resultsmentioning

confidence: 99%

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

et al. 2013

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An efficient and novel method for the synthesis in moderate to good yield (72%-84%) of a series of 3-amino-1-substituted-9,10-dihydrophenanthrene-2,4-dicarbonitriles 1-5 via one-pot multi-component reactions of aldehydes, malononitrile, 1-tetralone and ammonium acetate has been delineated. Cyclocondensation attempts of aminocyanophenanthrene derivatives 1, 2, 4 and 5 with acetic anhydride in the presence of conc. H 2 SO 4 failed and instead the diacetylamino derivatives 10-13 were obtained. All prepared compounds were structurally elucidated by various spectroscopic methods and X-ray crystallography. N,N-diacetylamino-derivatives of phenanthrene have shown good antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

et al. 2013

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“…Pyrans were readily obtained in good yields on treatment of ylidene derivatives of α-cyanochalcones with active methylene nitriles and active methylene ketones. Thus, benzylidene derivatives, aminomethylene and mercaptomethylene derivatives has been reported [170,235,236] to react with active methylene reagents to yield pyran derivatives [266][267][268][269][270][271][272].…”

Section: Synthesis Of Pyran Coumarin and Condensed Pyran Derivativesmentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

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including purines [7,8], pyrimidines [9], pyrazines [10] (some which are widely employed in the fluorescent dye industry [11]), imidazoles [12], biphenylenes [13], porphyrazines (which have great potential in optical sensor technology) [14] and diimines that are used as catalysts [15]. This review highlights the alkenyl nitrile chemistry with the focus on the utility of heterocyclic compounds. The synthesis and chemistry of the highly strained aryl nitrile is also briefly reviewed [16]. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into an structure, probably the use of a alkenyl nitrile analogue is the most direct one. The present review deals with the generation and synthetic uses of alkenyl nitriles and aryl nitriles formed in heterocyclic synthesis, and can be considered as an update of our revision published in 2007 on this topical [17]. Therefore, only references published from the second quarter of 2003 until the third quarter of 2010 are included, and the same restrictions to the literature coverage applied. Thus, only heterocycles compounds which are found applicability are considered. As previously, the present review is organized by the type of ring members and subdivided by the type of heterocycles fused compounds, including methods for their preparation and their synthetic uses. New developments in the utilities of some alkenyl nitriles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of alkenyl nitriles of active imines are discussed. The major methods and modifications are analyzed [18-21]. In this review, which covers the literature up to date, we describe the new and improved methods for the construction of the skeletons, with a particular emphasis on the four, five and six membered ring of heterocyclic compounds. Some of these procedures have clear technical advantages over older methods in terms of yield and versatility, but do not employ new chemistry in the construction of the ring systems. The

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Heterocyclen durch Michael‐Reaktionen, 8. Mitt. Reaktionen von Hydroxymethylentetralon mit Cyanessigsäurederivaten

Otto

Schmelz

1982

Archiv der Pharmazie

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Hydroxymethylentetralon (1) reagiert rnit Cyanessigsaurederivaten nicht wie andere 1,3-Dicarbonylverbindungen im Verhaltnis 1:1, sondern im Verhaltnis 1:2, wobei 10 bzw. 17 entstehen. Deren Strukturen werden geklart und ein Weg fur die Entstehung wird vorgeschlagen.Heterocycles by Michael Reactions, VIIIl): Reactions of (Hydroxymethy1ene)tetralone with Derivatives of Cyanoacetic Acid.(Hydroxymethy1ene)tetraIone 1 does not react with derivatives of cyanoacetic acid in a ratio 1:l like other 1,3-dicarbonyl compounds but in a ratio 1:2. These reactions yield compounds 10 and 17, whoses structures were elucidated mainly by spectroscopic methods. A reaction path is proposed.2-Arylidentetralone lassen sich mit aktivierten Methylengruppen z. B. in Malondinitril, Cyanessigestern u. a., glatt zu 4-Aryl-Benzo[h]chinolinonen umsetzen, wobei die Gesamtreaktion als eine Folge von Michael-Addition, Cyclisierung und z. T. Umlagerung angesehen werden ~u B~,~) .Der erste Schritt dieser Sequenz, die Michael-Addition und damit auch die Art des Endproduktes, hangt wesentlich von dem Substituenten an der exocyclischen Doppelbindung des s-cis fixierten a$-ungesattigten Systems ab, wie wir durch Vergleich der Reaktionsmoglichkeiten der 4-Arylidenpyrazolone rnit denen der 4-Dimethylaminomethylenpyrazolone zeigen konnten'). Wie sich dieser Effekt in derReihe der Tetralone auswirkt, untersuchten wir am Beispiel des nach Christo15) hergestellten 2-Hydroxymethylen-1-tetralons (l), woruber im folgenden benchtet werden soll. Bei 1 handelt es sich urn eine 1,3-Dicarbonylverbindung, die nach Aussage des 'H-NMR-Spektrums in Chloroform-Losung bevorzugt (> 95 %) in der Hydroxymethylenketon-Form 1111 vorliegt, wohingegen die Formylketon-11 bzw. Aldoenol-Form 111 keine Rolle zu spielen scheined).Reaktionen von anderen 1,3-Dicarbonylverbindungen rnit aktiven Methylenverbindungen sind zahlreich be~chrieben'-~). So reagiert Acetylaceton sowohl mit Malondinitril als auch mit Cyanacetamid zum 3-Cyan-4,6-dime thyl-Zpyridon (2)") und aus Acetessigester wird unter ahnlichen Bedingungen 3-Cyan-6-hydroxy-4-methyl-2-pyridon (3)") erhalten. Das 1 strukturell ahnlichere 2-Hydroxymethylencyclohexanon ergibt nach Sen-Gupta") mit Cyanacetamid das 3-Cyan-2-chinolon-Derivat 4. Wahrend diese Reaktionen uber eine 03654233/82/0606-0526 $ M.50/0

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Reaktionen von Arylidentetralonen mit Cyanessigs�urederivaten

Cited by 11 publications

References 2 publications

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Heterocyclen durch Michael‐Reaktionen, 8. Mitt. Reaktionen von Hydroxymethylentetralon mit Cyanessigsäurederivaten

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