N-Methyl-2-pyrrolealdehyde and N-Methyl-2-hydroxymethylpyrrole

Ryskiewicz, Edward E.; Silverstein, Robert M.

doi:10.1021/ja01651a066

Cited by 20 publications

(10 citation statements)

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“…Monocrotaline and retrorsine pyrroles were prepared from the parent alkaloids by the method of Mattocks (1969) and then were dissolved in freshly redistilled 1,2-dimethoxyethane. N-methyl-2-hydroxymethylpyrrole was prepared from N-methylpyrrole-2-aldehyde (Koch-Light Laboratories Ltd., Colnbrook, Bucks., U.K.) by the method of Ryskiewicz & Silverstein (1954). It was converted into the N-ethyl carbamate ester by the action of ethyl isocyanate (Koch-Light Laboratories Ltd.) under reflux.…”

Section: Methodsmentioning

confidence: 99%

Reaction of dihydropyrrolizines with deoxyribonucleic acids in vitro

White

Mattocks

1972

Biochemical Journal

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1. Thermal denaturation profiles of Escherichia coli DNA pretreated with monocrotaline pyrrole in vitro showed no difference from control DNA samples during heating. A substantial increase in the degree of renaturation during cooling of the pretreated DNA samples was observed. The degree of renaturation was dependent on the concentration of pyrrole used. 2. When rat liver DNA was pretreated with monocrotaline pyrrole there was a greater degree of renaturation after heat treatment than was found with E. coli DNA. 3. Equilibrium-density-gradient centrifugation in alkaline caesium chloride showed that DNA pretreated with monocrotaline pyrrole and heat denatured, renatured to a greater extent on quenching in ice than did untreated control DNA. The degree of renaturation was similar whether the initial treatment of the DNA with pyrrole was for 1 or for 15min. The reaction also appeared to be independent of pH between 5.5 and 9.0. 4. Retrorsine pyrrole was as effective as monocrotaline pyrrole in cross-linking the DNA, but monocrotaline pyrrole exposed to water for 5min before the addition of the DNA was ineffective. Pretreatment of E. coli DNA with synthetic bis-hydroxymethylpyrrole esters also caused renaturation after heat treatment. Monoesters were ineffective. 5. After treatment of rats with retrorsine, no cross-linking of the liver DNA could be demonstrated.

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Section: Methodsmentioning

confidence: 99%

Reaction of dihydropyrrolizines with deoxyribonucleic acids in vitro

White

Mattocks

1972

Biochemical Journal

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“…20,23) provide steric as well as electronic constraints which are not completely understood; 20 " Chemical shifts relative to TMS in CDClg. 6 Satisfactory elemental analyses were reported for all compounds in the table.…”

Section: References and Notesmentioning

confidence: 99%

“…Table II Conversion of Methylenedioxy Olefins to Aminoindenes " Chemical shifts relative to TMS of free base in (CD3)2CO. 6 Chemical shifts relative to TMS of HC1 salts in CDC13. 'A 16% yield is obtained if the reaction is carried out as described in the Experimental Section.…”

Section: References and Notesmentioning

confidence: 99%

Vilsmeier-Haack cyclizations. Synthesis of 2-substituted 3-dimethylamino-5-6-methylenedioxyindenes and the corresponding indanones

Witiak¹,

Williams²,

Kakodkar³

1974

J. Org. Chem.

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In the presence of the Vilsmeier-Haack reagent, suitably activated styrene analogs afford previously unreported 2-substituted 3-dimethylamino-5,6-methylenedioxyindenes. The indenes were hydrolyzed to the corresponding indanones. This constitutes a new synthesis of indanones. Cinnamaldehydes are also obtained under Vilsmeier-Haack conditions. Reaction conditions and electronic and other structural requirements which govern the formation of cinnamaldehydes and aminoindenes are discussed. Selected cinnamaldehydes were shown to have the E configuration by X-ray crystallography. Aminoindenes result from cyclization of Vilsmeier-Haack intermediates (4) having the Z configuration while aldehydes result from Vilsmeier-Haack intermediates (4) having the E configuration.

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“…Un tel resultat a Cti: comment6 par McGlynn et coll. (5). Enfin des mesures de polarisation aux differentes longueurs d'onde de l'emission, il dkcoule une valeur moyenne P = +0.2 ( fig.…”

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Pyrrole Chemistry. XIV. Some Chemical and Physical Properties of 3-Pyrrolecarbaldehyde and 1-Methyl-3-pyrrolecarbaldehyde

Anderson¹,

Nagy²

1972

Can. J. Chem.

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3-Pyrrolecarbaldehyde (1) has been prepared on an increased scale. A general survey of the physical and chemical properties of the 3-aldehyde and I-methyl-3-pyrrolecarbaldehyde has been carried out. The results indicate similar chemical properties to those of the corresponding 2-aldehydes. The physical properties are generally predictable on the basis of earlier studies.Le pyrrolecarbaldthyde-3 (I) a tte prepare sur une plus grande echelle. Une revue generale des proprittts physiques et chimiques de l'aldehyde-3 et du methyl-1 pyrrolecarbaldthyde-3 a ett mente a bien. Les rtsultats indiquent des proprietes chimiques semblables a celles des aldthydes-2 correspondants. Les proprittes physiques sont en general previsibles en se fondant sur les etudes precedentes.

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N-Methyl-2-pyrrolealdehyde and N-Methyl-2-hydroxymethylpyrrole

Cited by 20 publications

References 0 publications

Reaction of dihydropyrrolizines with deoxyribonucleic acids in vitro

Reaction of dihydropyrrolizines with deoxyribonucleic acids in vitro

Vilsmeier-Haack cyclizations. Synthesis of 2-substituted 3-dimethylamino-5-6-methylenedioxyindenes and the corresponding indanones

Pyrrole Chemistry. XIV. Some Chemical and Physical Properties of 3-Pyrrolecarbaldehyde and 1-Methyl-3-pyrrolecarbaldehyde

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