Effect of Different Substituents on Amine-imine Tautomerism of 2-Amino-4-methylthiazole Derivatives

Hyengoyan, A. P.; Eliazyan, K. A.; Pivazyan, V. A.; Khazaryan, E. A.; Dovlatyan, V. V.

doi:10.1007/s10593-005-0280-7

Cited by 2 publications

(1 citation statement)

References 3 publications

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“…Because the enamine–imine tautomerism is fast in the NMR time scale, only average broad signal at 3.4 ppm was observed in the 1 H NMR spectrum of 1 . The analysis of both 1 H NMR and 13 C NMR spectra suggests that the studied diazepine exists mainly in the bis‐imine tautomeric form 1a in both CDCl 3 and DMSO‐ d 6 solutions.…”

Section: Resultsmentioning

confidence: 94%

Theoretical and experimental ¹⁵N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system

Semenov

Samultsev

Rulev

et al. 2015

Magnetic Reson in Chemistry

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The tautomeric structure of 4-trifluoromethyl[b]benzo-1,4-diazepine system in solution has been evaluated by means of the calculation of (15)N NMR chemical shifts of individual tautomers in comparison with the averaged experimental shifts to show that the enamine-imine equilibrium is entirely shifted toward the imine form. The adequacy of the theoretical level used for the computation of (15)N NMR chemical shifts in this case has been verified based on the benchmark calculations in the series of the push-pull and captodative enamines together with related azomethynes, which demonstrated a good to excellent agreement with experiment.

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Section: Resultsmentioning

confidence: 94%

Theoretical and experimental ¹⁵N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system

Semenov

Samultsev

Rulev

et al. 2015

Magnetic Reson in Chemistry

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Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution

Pankova¹,

Golubev²,

Khlebnikov³

et al. 2016

Beilstein J. Org. Chem.

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2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the ratio of these tautomers. Isomers with the alkyl group in the endocyclic position can be obtained from N-methyl(ethyl)thioureas. 2D NMR spectroscopy and DFT calculations rationalize experimental results.

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Effect of Different Substituents on Amine-imine Tautomerism of 2-Amino-4-methylthiazole Derivatives

Cited by 2 publications

References 3 publications

Theoretical and experimental ¹⁵N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system

Theoretical and experimental ¹⁵N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system

Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution

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Effect of Different Substituents on Amine-imine Tautomerism of 2-Amino-4-methylthiazole Derivatives

Cited by 2 publications

References 3 publications

Theoretical and experimental 15N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system

Theoretical and experimental 15N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system

Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution

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Theoretical and experimental ¹⁵N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system

Theoretical and experimental ¹⁵N NMR study of enamine–imine tautomerism of 4‐trifluoromethyl[b]benzo‐1,4‐diazepine system