Imino–enamine tautomerism and dynamic prototropy in 1-imino-3-amino-1H-indens

Mukano, Yoko; Mizuno, Mai; Takanashi, Yuriko; Suzuki, Masatatsu; Wakabayashi, Hidetsugu; Teramae, Hiroyuki; Kobayashi, Keiji

doi:10.1016/j.tet.2009.11.076

Cited by 6 publications

(6 citation statements)

References 18 publications

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“…Tautomeric effects taking place in the protonated form of drotaverine are also complex and may involve high differences of log D ow values. Similar dynamic interconversion of the imino-enamine forms was very recently revealed by temperature-dependent 1 H-NMR spectra [15]. In Fig.…”

Section: Drotaverinesupporting

confidence: 81%

Deviation from van't Hoff dependence in RP‐LC induced by tautomeric interconversion observed for four compounds

Galaon

David

2011

J of Separation Science

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The most encountered situations in reversed-phase liquid chromatography for temperature dependence of retention are those obeying the linear equation known as the van't Hoff plot. When studying compounds that are involved in structural modifications, it is likely that the temperature dependences of their retention factors do not follow this rule. It is the aim of this paper to report some particular cases when compounds involved in tautomeric interconversion have a different retention behavior with temperature: a deviation from the linearity of ln k on 1/T, or, in certain temperature ranges, temperature increase leading to a retention increase. Examples of compounds exhibiting deviation from the van't Hoff temperature dependence are piroxicam, drotaverine, vincamine, and epivincamine. A simple thermodynamic model relying on tautomeric equilibria in mobile phase is proposed for these compounds, which gives a polynomial dependence between ln k and 1/T.

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Section: Drotaverinesupporting

confidence: 81%

Deviation from van't Hoff dependence in RP‐LC induced by tautomeric interconversion observed for four compounds

Galaon

David

2011

J of Separation Science

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“…This observation suggests that only the latter proton participates in the intermolecular hydrogen bonding with DMSO. A similar dynamic prototropic behavior accompanied by the carbon–carbon bond rotation has been found for an analogous perimidine system including the intramolecular NH----O=C hydrogen bonding system [25] and for a pyridine compound including the NH---N hydrogen bonding system [26]. …”

Section: Resultssupporting

confidence: 62%

Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin

et al. 2012

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Spiro-N,N-ketal 5, consisting of a phthaloperine heterocyclic ring and a naphtha[1,8-ef][1,4]diazepine ring, was obtained along with spiro-N,N-ketal 2 via 2,2-condensation in the reaction of ninhydrin with naphthalene-1,8-diamine. Their molecular structures were elucidated by X-ray crystal structural analysis. Aside from these spiro compounds, the diazapleiadiene compound 3 formed by 1,2-condensation and the 1,4-isoquinolinedione compound 4 arising from ring expansion were isolated. When isatin was reacted with naphthalene-1,8-diamine, spiro-N,N-ketal 6 and the two 1H-perimidine-based compounds 7 and 8 were isolated. Compound 8 was revealed to undergo a fast dynamic prototropic tautomerization in solution. Plausible mechanisms of the formation of the products are proposed.

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Section: Imine-amine Tautomerismmentioning

confidence: 99%

“…If, however, the imine-enamine tautomeric system is incorporated in the 1,3-indandione skeleton and configurational uncertainties are deleted, the tautomerism can be studied readily (Scheme 5.16) [53]. [53]. The imino-enamino tautomerism of β-imino sulfoxides was studied, showing in all instances the imino form [Ar-S(=O)-CH 2 -C(R )=NR] as the predominant tautomer, independent of substitution [54].…”

Section: Imine-amine Tautomerismmentioning

confidence: 99%

NMR Spectroscopic Study of Tautomerism in Solution and in the Solid State

Kleinpeter

2013

Tautomerism

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Imino–enamine tautomerism and dynamic prototropy in 1-imino-3-amino-1H-indens

Abstract: Imino-enamine tautomerism and dynamic prototropy in 1-imino-3-amino-1H-indens

Cited by 6 publications

References 18 publications

Deviation from van't Hoff dependence in RP‐LC induced by tautomeric interconversion observed for four compounds

Deviation from van't Hoff dependence in RP‐LC induced by tautomeric interconversion observed for four compounds

Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin

NMR Spectroscopic Study of Tautomerism in Solution and in the Solid State

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