Hydrazones

Бузыкин, Б. И.; Bystrykh, N. N.; Stolyarov, A. P.; Flegontov, S. A.; Зверев, В. В.; Kitaev, Yu. P.

doi:10.1007/bf00479580

Chem Heterocycl Compd

1976

DOI: 10.1007/bf00479580

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Hydrazones

Б. И. Бузыкин¹,

N. N. Bystrykh²,

A. P. Stolyarov³

et al.

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Cited by 2 publications

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“…The 1 H NMR spectra show the hydroxyl group proton at 9.52-10.32 ppm and the proton on the carbon of the azomethine fragment as a singlet at 8.24-8.29 ppm [2].…”

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confidence: 99%

Synthesis of 2-(2-hydroxybenzyl)phthalazin-1(2H)-ones

Osyanin

Ивлева

Klimochkin

2011

Chem Heterocycl Comp

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It is known that reaction of naphthalene series o-methylenequinones, generated in situ from 1-dimethylaminomethyl-2-naphthol, and phthalazin-1(2H)-ones form the Diels-Alder heteroreaction adducts 5,15a-dihydro-6H, 8H-naphtho[1',2':5,6]oxazino[2,3-a]phthalazin-5-ones [1]. At the same time, in the case of o-methylenequinones generated from the salicyl alcohols 1a-c, there are obtained, rather than the expected 6H,8H-phthalazino[1,2-b][1,3]benzoxazines, the products of Michael 1,4-addition, i.e. the 2-(2-hydroxybenzyl)phthalazin-1(2H)-ones 2a-c. OH R OH CH 2 O R N NH O N N O OH R N H O N O R a R = H, b R = Br, c R = COMe о-xylene, 145°C 2a-c 1a-c -H 2 OThe IR spectra of compounds 2a-c show the presence of carbonyl stretching bands for the heterocycle fragments in the range 1628-1632 cm -1 . The hydroxyl group corresponds to a broad absorption band in the range 2800-3300 cm -1 . The retention of intense C=N stretching bands at 1582 cm -1 also provides an evidence about the

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“…The 1 H NMR spectra show the hydroxyl group proton at 9.52-10.32 ppm and the proton on the carbon of the azomethine fragment as a singlet at 8.24-8.29 ppm [2].…”

mentioning

confidence: 99%

Synthesis of 2-(2-hydroxybenzyl)phthalazin-1(2H)-ones

Osyanin

Ивлева

Klimochkin

2011

Chem Heterocycl Comp

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Synthese von [1,2,4]Triazolo [1,5‐a]chinazolinen. Ableitung der Konformation von Substituenten mit Hilfe der ¹³C‐NMR.‐Spektroskopie

Heckendorn

Winkler

1980

Helvetica Chimica Acta

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Synthesis of [1,2,4]Triazolo [1,5-ajquinazolines. Assignment of the Conformation of Substitnents with the Aid of I3C-NMR. Spectroscopy SummaryThe synthesis of [ 1,2,4Jtriazolo [ 1,5-a]quinazolines by condensation of 2-hydrazinobenzoic acid with N-cyano-imidates is reported. The preferred conformation of substituents at C(5), e.g. N (CH,),, N (CH,)NH,, N (CH,)OH, relative to the aromatic system is deduced with the aid of 13C-NMR. chemical shifts and proton nuclear Overhauser effect experiments.In vorangegangenen Arbeiten haben wir die Abhangigkeit der chemischen Verschiebungen im '3C-NMR.-Spektrum von der Orientierung von Substituenten in Indolinen und Tetrahydrochinolinen [ 1 J sowie in Spiro [cyclopropan-l', 9fluorenen] [2] untersucht. Diese Abhangigkeit eignet sich, urn die bevorzugte Konformation von Substituenten aufzuklaren. Im folgenden wird uber eine Anwendung berichtet, die bei der Arbeit an einer neuen Triazolo-chinazolin-Synthese gefunden wurde. Synthese der Verbindungen. -In der Literatur findet sich bis jetzt ein einziger Hinweis auf das [I, 2,4JTriazolo [ 1,5-aJchinazolin-Ringsystem. Im Jahre 1949 setzten Cook et al. [3] 3-Amino-1,2,4-triazol mit 2-Oxocyclohexan-1-carbonsaure-athylester und 2-Hydroxymethyliden-cyclohexanon zu tricyclischen Verbindungen urn. Allerdings liessen die Autoren offen, ob dabei [ 1,2,4JTriazolo [ 1,5-~]chinazolin-oder [ 1,2,4]Triazolo [4,3-a]chinazolin-Derivate vorlagen. Aromatisierungsversuche mit diesen Verbindungen gelangen nicht. Wir haben nun gefunden, dass das [I, 2,4JTriazolo [ 1,5-a]chinazolin-Ringsystem sich auf eindeutige Weise in einer Eintopfreaktion aus 2-Hydrazinobenzoesaurehydrochlorid (1) in guter Ausbeute herstellen lasst. In Analogie zu Arbeiten von Wright [4], wonach entsprechende Pyrazolo [ 1,5-a]chinazolin-Systeme durch Umsatz von 1 mit 3-Aminocrotononitril oder 2-Cyano-3-athoxy-acrylsaure-athylestern I)

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Hydrazones

Cited by 2 publications

References 12 publications

Synthesis of 2-(2-hydroxybenzyl)phthalazin-1(2H)-ones

Synthesis of 2-(2-hydroxybenzyl)phthalazin-1(2H)-ones

Synthese von [1,2,4]Triazolo [1,5‐a]chinazolinen. Ableitung der Konformation von Substituenten mit Hilfe der ¹³C‐NMR.‐Spektroskopie

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Hydrazones

Cited by 2 publications

References 12 publications

Synthesis of 2-(2-hydroxybenzyl)phthalazin-1(2H)-ones

Synthesis of 2-(2-hydroxybenzyl)phthalazin-1(2H)-ones

Synthese von [1,2,4]Triazolo [1,5‐a]chinazolinen. Ableitung der Konformation von Substituenten mit Hilfe der 13C‐NMR.‐Spektroskopie

Contact Info

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Synthese von [1,2,4]Triazolo [1,5‐a]chinazolinen. Ableitung der Konformation von Substituenten mit Hilfe der ¹³C‐NMR.‐Spektroskopie