Studies on Monoamine Oxidase Inhibitors. II. A Note on the Reaction between 1,2-Diethylhydrazine and Acetaldehyde.

Eberson, Lennart; Persson, Kaj; Thorkilsen, B.; Halvarson, Hans; Nilsson, Lennart

doi:10.3891/acta.chem.scand.18-0721

Cited by 5 publications

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“…§ In this work, we attempted to synthesise some compounds of the above types. The syntheses of 2,3,4,5-tetraalkyl-1,3,4oxadiazolidines C in 60-70% yields by the reactions of N,N'dimethylhydrazine with aldehydes RCHO (R = H, Me, Pr or Bu) 9 and N,N'-diethylhydrazine with acetaldehyde 10 were described previously. However, we found that pyrazoline 1 was formed in the reaction of N,N'-diisopropylhydrazine with acetaldehyde under the same conditions 10 instead of expected product C (R = Pr i ) (Scheme 2).…”

Section: 1070/mc2002v012n05abeh001626mentioning

confidence: 99%

“…Indeed, pyrazoline 1 can be directly prepared by the reaction with crotonaldehyde (Scheme 2). It is interesting that a pyrazoline byproduct (in up to 5% yield) was detected in the reaction of less sterically hindered sym-diethylhydrazine, whereas the corresponding oxadiazolidine 9 is the main product (Scheme 3). This is a general reaction.…”

Section: 1070/mc2002v012n05abeh001626mentioning

confidence: 99%

“…‡ Compounds of the type C (R = Me, Et) were described. 9 § Pyrazolidines D (R = H, PhCO), 11 E (X = CH 2 , R = CO 2 Et), 12 (X = = Me 2 C, R = CO 2 Et) 13,14 and F (R = H, R' = Me) 15 were described. (Pr i NH) 2 C H 4 J (H3)(H5) = -1.5 Hz).…”

Section: 1070/mc2002v012n05abeh001626mentioning

confidence: 99%

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Sterically hindered nitrogen inversion in five-membered cyclic hydrazines

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Section: 1070/mc2002v012n05abeh001626mentioning

confidence: 99%

Section: 1070/mc2002v012n05abeh001626mentioning

confidence: 99%

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Sterically hindered nitrogen inversion in five-membered cyclic hydrazines

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Über Hydrazin‐acetale

Zinner¹,

Kliegel²,

Ritter³

et al. 1966

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Aus den Instituten fur Pharmazeutische Chemie der Universitaten Marburg (Lahn) und Miinster (Westf.)*) (Eingegangen am 7. Dezember 1965) 1.1.2-Trialkyl-hydrazine bilden mit Formaldehyd Bis-trialkylhydrazino-methan-Verbindungen (,,Hydrazinale") 2, die mit Acylchloriden zu Acylhydrazinen 3 und Chlormethyl-trialkylhydrazinen 4 aufspalten. Bei der Einwirkung hdherer Aldehyde wurden En-hydrazine gefaRt. In Gegenwart anderer nucleophiler Komponenten geben 1.1.2-Trialkyl-hydrazine mit Formaldehyd N.N-, N . 0und N.S-Acetale (13, 16, 14, 17, 18, 15), deren Acylchlorid-Spaltung zu Chlormethyl-trialkyl-hydrazinen und dem Acylderivat der schwacher nucleophilen Komponente fiihrt. 1.2-Diisopropyl-hydrazin lie6 sich rnit Formaldehyd zu einem 1.3.4-Oxadiazolidin-Derivdt 29a, rnit Isobutyr-und 2-Athyl-butyraldehyd dagegen zu Hexahydro-l.2.4.5tetrazin-Derivaten 32 umsetzen. In gleicher Weise, wie sich aus sek. Aminen rnit Formaldehyd symmetrische N.N-Acetale1) (Aminalez)) 1 bilden, lassen sich aus 1.1.2-Trialkyl-hydrazinen3) und Forrnaldehyd Bis-trialkylhydrazino-methan-Derivate (,,Hydrazinale") 2 erhaltens. Diese gleichen den Aminalen auch im reaktiven Verhalten insofern, als sie sich wie diese rnit Acylchloriden leicht aufspalten lassen. In einer solchen Spaltungsreaktion wurde vor einigen Jahren von Bohme und Hartkes) ein einfacher und glatter Weg zur Herstellung von Carbimoniumhalogeniden (,,a-halogenierten Aminen") gefunden. Mit unseren Hydrazinalen tritt die Reaktion ebenfalls sehr leicht ein : wir isolierten nach R,N R g -(CH3)N 1 2a-d 3a-d 4a-d A a: R = CH, b: R = C2H, c: Rz = 3 d: R2 = -0

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Studies on Monoamine Oxidase Inhibitors. II. A Note on the Reaction between 1,2-Diethylhydrazine and Acetaldehyde.

Cited by 5 publications

References 0 publications

Sterically hindered nitrogen inversion in five-membered cyclic hydrazines

Sterically hindered nitrogen inversion in five-membered cyclic hydrazines

Oxadiazoles

Über Hydrazin‐acetale

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