NMR spectral study of the structure of 2-amino-4-thiazolinones

Рамш, С. М.; Smorygo, N. A.; Храброва, Е. С.; Гинак, А. И.

doi:10.1007/bf00542789

Cited by 6 publications

(10 citation statements)

References 7 publications

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“…Resonating signals at δ 7.46‐7.37 ppm in 1 H NMR was associated with the olefinic proton ( H 7 ). The chemical shift value observed for this proton was higher than expected for 5E isomer and was mainly because of anisotropic effect of CO present in the vicinity of this proton . Further, a proton present in the vicinity of sulfur would resonate at lower δ value due to less deshielding effect exerted by sulfur, which was also not observed in present case .…”

Section: Resultsmentioning

confidence: 91%

“…Therefore, these compounds exist only in one configurational isomer 2Z,5Z. The existence of two isomeric forms in terms of CN configurational isomers was supported by the presence of two signal sets when the spectra were recorded in DMSO which is also conferring with the literature . The predominance of isomer was assessed by integrating the singlets observed for protons related with methoxy (OCH 3 ) and pyrazole at 25°C.…”

Section: Resultsmentioning

confidence: 99%

“…Two configurational isomers in terms of E and Z at the imino form of 2-arylimino-4-thiazolidinone were very well-cited in the literature. [43] In case of 3a, single set of signals was observed, however, for 3b, two signal sets were observed for CH 2 , NH, OCH 3 , and aryl protons as shown in (Figure 1).…”

Section: Chemistrymentioning

confidence: 88%

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Thiazolidine‐4‐one clubbed pyrazoles hybrids: Potent α‐amylase and α‐glucosidase inhibitors with NLO properties

Kumar

Duhan

Sindhu

et al. 2019

Journal of Heterocyclic Chem

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Molecular hybrids based on thiazolidin‐4‐one and pyrazolyl pharmacophore (THZP) as new antidiabetic agents were synthesized. Two sets of signals came into view in 1H NMR of THZP8‐THZP14 exhibited the presence of a configurational isomeric mixture of 2E,5Z (38.24%‐41.58%) and 2Z,5Z isomers (58.42%‐61.76%), which was further endorsed by density functional theory (DFT) studies. All the compounds exhibit promising nonlinear optical properties (NLO). Further, the biological potential of THZPs was explored in terms of α‐amylase and α‐glucosidase inhibition. DFT‐based descriptors were calculated to describe the reactivity, and a relationship was developed with biological activities. THZP9 and THZP14 showed remarkable inhibition of α‐amylase and α‐glucosidase with IC50 9.90μM and 4.84μM, respectively, as compared with standard drug acarbose.

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 99%

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Thiazolidine‐4‐one clubbed pyrazoles hybrids: Potent α‐amylase and α‐glucosidase inhibitors with NLO properties

Kumar

Duhan

Sindhu

et al. 2019

Journal of Heterocyclic Chem

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“…This phenomenon was first detected by UV spectroscopy [19] and believed to be caused by a proton transfer between nitrogen atoms (amino–imino tautomerism), however, contradictory information on the equilibrium ratio of tautomers exist [15,18,20–23]. ( E / Z )-Isomerization of the exocyclic C=N bond of the single imino form was suggested as the cause for the dynamic effect as well [24–25]. In addition, this process complicates the interpretation of NMR spectra of thiazolidines and is a likely source of misinterpretations.…”

Section: Introductionmentioning

confidence: 99%

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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“…A further confirmation of substitution at the exocyclic nitrogen atom is the relatively low frequency for the C (2) =N (3) bond absorption (1590-1595 cm -1 ) in the IR spectra [9,10]. 2methylamino-1,3-thiazol-4(5H)-one [14] and its 5-benzylidene analog [15]. a pseudothiohydantoin [11,8] and its 5-aryl derivatives [12].…”

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confidence: 99%

2-Amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spirodioxane compounds in the Mannich reaction

Рамш¹,

Ivanenko²,

Medvedskiy³

et al. 2006

Chem Heterocycl Compd

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It was found that the aminomethylation of 2-amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spiro analogs using primary amines is accompanied by cyclization at the amidine fragment of the molecule with annelation of a tetrahydrotriazine ring. When using secondary amines the aminomethylation occurs at the exocyclic nitrogen atom.Keywords: 2-amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one, 2-'amino-2-aryl(hetaryl)spiro-[1,3-dioxan-5,5'(4'H)-1',3'-thiazol]-4'-ones, 5-methyl-and 2-amino-5-ethyl-1,3-thiazol-4(5)-ones, aminomethylation.We have previously been able to prepare a 5,5-bis(hydroxymethyl) derivative of 2-amino-1,3-thiazol-4(5H)-one (pseudothiohydantoin) (1a) [1] and synthesize a series of spiro-[1,3-dioxan-5,5'(4'H)-1',3'-thiazole] derivatives (2a-e) from it [2]. Compound 1a is a "truncated" (fragmented) part of the compound 3a molecule which shows high biological activity [3]. This encouraged us to develop a novel method for the preparation of active compound 3a by the aminomethylation of the bis(hydroxymethyl) derivative 1a. This was particularly in view of the fact that the preparation of compound 3a, initially proposed via the direct aminomethylation of pseudothiohydantoin [3,4] is accompanied by the formation of a side reaction product and the yield of the target compound 3a does not exceed 30%. It also seemed suitable for developing a method of preparing homologs of compound 3a through the variation of the amino component in the aminomethylation reaction of compound 1a.With the aim of subsequently studying the biological activity of the newly obtained compounds and revealing a structure-activity relationship we have also synthesized in the work the monohydroxymethyl and spiro analogs of compound 3a using the 1b,c or spiro compounds 2a-e as substrates in the Mannich reaction and tert-butylamine or methylamine as the amino component. The aminomethylation of substrate 1a with secondary cyclic amines also gave the Mannich bases 5a,b, differing from compound 3a in the acyclic structure of the aminomethyl fragment of the molecule. Finally, the hydroxymethylation of the thiazolo[3,2-a]pyrimidine derivative 6 gave compound 7 as the "desaminated" analog of compounds 3a. __________________________________________________________________________________________

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NMR spectral study of the structure of 2-amino-4-thiazolinones

Cited by 6 publications

References 7 publications

Thiazolidine‐4‐one clubbed pyrazoles hybrids: Potent α‐amylase and α‐glucosidase inhibitors with NLO properties

Thiazolidine‐4‐one clubbed pyrazoles hybrids: Potent α‐amylase and α‐glucosidase inhibitors with NLO properties

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

2-Amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spirodioxane compounds in the Mannich reaction

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