Functionalized enamines—XXII

Manhas, M. S.; Brown, J; Pandit, U. K.; Houdewind, P.

doi:10.1016/0040-4020(75)80178-5

Cited by 14 publications

(2 citation statements)

References 34 publications

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“…It is clear that all nitrogens are sp 2 hybridized which may point to extensive delocaliza- [17], failed. On the other hand, dioxime 5 afforded α-hydrazonopropionitrile 8 when treated with acetic acid (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

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Studies with 2-(Arylhydrazono)aldehydes: Synthesis and Chemical Reactivity of Mesoxalaldehyde 2-Arylhydrazones and of Ethyl 2-Arylhydrazono-3-oxopropionates

Makhseed

Hassaneen

Elnagdi

2007

Zeitschrift Für Naturforschung B

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The coupling reaction of 3-(dimethylamino)acrolein (2a) and ethyl 3-(dimethylamino)acrylate (2b) with arenediazonium chlorides afforded the 2-(arylhydrazono)aldehydes 1a -e. Compounds 1a, b reacted with hydroxylamine hydrochloride to yield the oximes 4a, b. The dioxime 5 was obtained from reaction of 1a with an excess of hydroxylamine hydrochloride. This dioxime afforded the 1,2,3-triazole carbonitrile 6 when treated with acetic anhydride, while α-hydrazono propionitrile 8 was obtained when 5 was treated with acetic acid. Compounds 1a -e could be utilized for the synthesis of a variety of pyrazoles and arylazolopyrimidines via reaction with hydrazines, haloketones and aminoazoles, respectively.

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Section: Resultsmentioning

confidence: 99%

“…The data were collected at a temperature of 20±1 • C using the ω scanning technique to θ max = 26.02 • . The structure was solved by Direct Methods using SIR 92 and refined by full-matrix least-squares [17]. Non-hydrogen atoms were refined anisotropically.…”

Section: Crystallographic Analysismentioning

confidence: 99%