Stereochemistry of grignard reactions on some conformationally mobile δ-keto esters

Colantoni, A; Maio, Giorgio Di; Vecchi, Elisabetta; Zeuli, E.; Quagliata, C.

doi:10.1016/s0040-4020(01)93593-8

Cited by 11 publications

(1 citation statement)

References 11 publications

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“…Our value for that angle (68.6°) agrees with the results obtained by potential energy calculations for the eis tetrahydro-5,6dimethyl-6-phenyl-2H-pyran-2-one (Colantoni et al, 1978). Our value for that angle (68.6°) agrees with the results obtained by potential energy calculations for the eis tetrahydro-5,6dimethyl-6-phenyl-2H-pyran-2-one (Colantoni et al, 1978).…”

Section: The Lactone Ringsupporting

confidence: 89%

The molecular structure of trans 3,6-dimethyl-6-phenyltetrahydro-2-pyrone in the crystal

Maio¹,

Portalone²,

Spagna³

et al. 1986

Zeitschrift Für Kristallographie - Crystalline Materials

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The molecular structure of the title compoimd has been determined by X-ray crystaUography. The crystals are monoclinic, space group P2Ja, with a = 10.818(1), b = 9.062(1). c = 11.822(1) k, ß = 91.87(1)°, Z = 4. The structure has been solved by direct methods and refined by least-squares techniques to R = 0.0469 on 1684 counter intensities. Crystallographic data analysis demonstrates that in the solid State the ölactone adopts a distorted half-chair conformation due to the planarity of the carbonyl group, and the benzene ring is in the axial position. The mutual orientation of the lactone ring and the phenyl substituent obtained by Potential energy calculations and by NMR spectroscopic analysis is in agreement with the results of the present study.

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Section: The Lactone Ringsupporting

confidence: 89%

The molecular structure of trans 3,6-dimethyl-6-phenyltetrahydro-2-pyrone in the crystal

Maio¹,

Portalone²,

Spagna³

et al. 1986

Zeitschrift Für Kristallographie - Crystalline Materials

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ChemInform Abstract: STEREOCHEMISTRY OF GRIGNARD REACTIONS ON SOME CONFORMATIONALLY MOBILE Δ‐KETO ESTERS. THE EFFECTS OF CHANGING SOLVENT AND REACTANT

Colantoni¹,

Maio²,

Vecchi³

et al. 1978

Chemischer Informationsdienst

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Beiträge zur Chemie des Indols, XII. Synthesen eserinähnlicher Verbindungen, III; Neue an N‐1 und N‐8 substituierte Derivate des Desoxyeserolins sowie eine neue Synthese des Eserethols

Rosenmund

Sadri

1979

Liebigs Ann. Chem.

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Die Behandlung der 3-Methyl-4-phenylhydrazonobutansaure-ethylester 1 rnit H WEthanol liefert in guten Ausbeuten die Furoindolone 2. Die Reaktion von 2 rnit primaren Aminen ergibt ohne Nebenprodukte die Pyrroloindolone 3. Weiterhin werden Umsetzungen von 2 rnit komplexen Hydriden und rnit Grignard-Verbindungen beschrieben. Aus 2g erhalt man rnit LiAlH4 in quantitativer Ausbeute Eserethol (4e). Contributions to the Chemistry of Indole, XII1). -Syntheses of Compounds Similar to Eserine, 111; New Derivatives of Deoxyeseroline Substituted at N-1 and N-8 and a Novel Synthesis of EseretholeTreatment of the ethyl 3-methyl-4-phenylhydrazonobutanoates 1 with HCl/ethanol gives the furoindolones 2 in good yields. Reaction of 2 with primary amines furnishes the pyrroloindolones 3 without by-products. Furthermore, reactions of 2 with complex hydrides and with Grignard compounds are described. Eserethole (4e) has been obtained in quantitative yield by reaction of Zg with LiAIH4.Vor einigen Jahren berichteten wir iiber eine neue Synthese des Desoxye~erolins~) (4a), desgleichen uber eine Totalsynthese des Thioeserins4), worin der phenolische Sauerstoff des Eserins gegen Schwefel ausgetauscht ist. Diese Mercaptogruppe kann die In-vivo-Ringoffnung zum quartaren 3H-Indoliumion beeinflussen, was fur den postulierten Mechanismus der Acetylcholinesterase-Hemmung von Bedeutung ist5). Jiingere Synthesen, welche auf die Darstellung eserinahnlicher Verbindungen zielen, zeigen, da13 weiterhin Interesse an dieser Verbindungsklasse besteht6).Wir entwickeln hier einen Syntheseweg, der die Substituenten an N-1 und N-8 weitgehend beliebig und unabhangig voneinander abzuwandeln gestattet. Der Ubergang von 2 nach 3 verlauft ungewohnlich glatt, 3 enthalt bereits das vollstandige Eserinskelett. Lediglich die Darstellung von 2a war bisher3) relativ umstandlich, erforderte unter anderem die Fallung des als Katalysator verwendeten Zinn(I1)-chlorids mit Schwefelwasserstoff und ergab nur maljige Ausbeuten. Wir fanden jetzt, dalj das Hydrazon l a in mit HCl gesattigtem Ethanol in ca. einer halben Stunde cyclisiert. Die *) Korrespondenz bitte an diesen Autor richten.

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Stereochemistry of grignard reactions on some conformationally mobile δ-keto esters

Cited by 11 publications

References 11 publications

The molecular structure of trans 3,6-dimethyl-6-phenyltetrahydro-2-pyrone in the crystal

The molecular structure of trans 3,6-dimethyl-6-phenyltetrahydro-2-pyrone in the crystal

ChemInform Abstract: STEREOCHEMISTRY OF GRIGNARD REACTIONS ON SOME CONFORMATIONALLY MOBILE Δ‐KETO ESTERS. THE EFFECTS OF CHANGING SOLVENT AND REACTANT

Beiträge zur Chemie des Indols, XII. Synthesen eserinähnlicher Verbindungen, III; Neue an N‐1 und N‐8 substituierte Derivate des Desoxyeserolins sowie eine neue Synthese des Eserethols

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