1H, 13C, 15N NMR, ESI mass spectral and single crystal X-ray structural characterization of three spiro[pyrrolidine-2,3′-oxindoles]

Laihia, Katri; Valkonen, Arto; Kolehmainen, Erkki; Antonov, Andrey A.; Zhukov, D. V.; Fedosov, Ivan V.; Nikiforov, Vladimir

doi:10.1016/j.molstruc.2006.03.095

Cited by 6 publications

(3 citation statements)

References 8 publications

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“….Recently, Laihia et al[407] have reported the 1 H, 13 C,15 N NMR, ESI mass, and single-crystal X-ray structural characterization of three spiro[pyrrolidine-2,3´-oxindoles](40).…”

mentioning

confidence: 99%

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

Marek¹,

Lyčka²,

Kolehmainen³

et al. 2007

COC

131

110

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Since our previous review article (Curr. Org. Chem. 2002, 6, 35), significant improvements and an array of 15 N NMR applications in structural analysis have been published. This report aims to update coverage of improvements in methodology and various types of applications published over the period 2001 -2005. Substantial progress in cryogenic probe technology and the commercial availability of cryoprobes have facilitated the measurement of 15 N NMR parameters.The number of solid-state applications has increased significantly during the past few years. In contrast to our previous review, this article covers 15 N solid-state studies. The 15 N NMR chemical shifts of organic molecules are routinely measured by using cross-polarization magic-angle spinning (CP/MAS) techniques. The principal values of the chemical shift tensors can also be determined. 1 H-15 N and 2 H-15 N distance measurements made by means of 1 H detection are currently used in NMR crystallography.User friendly quantum chemical programs allow for the routine calculation of 15 N chemical shielding and indirect spinspin coupling constants, especially using density functional theory (DFT).Applications of 15 N NMR spectroscopy in various fields of chemistry are summarized here. Major sections represent tautomerism, complexation, protonation, and hydrogen bonding. The other topics comprise N-alkylation, N-oxidation, regioisomerism, and changes in configuration or conformation.

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“….Recently, Laihia et al[407] have reported the 1 H, 13 C,15 N NMR, ESI mass, and single-crystal X-ray structural characterization of three spiro[pyrrolidine-2,3´-oxindoles](40).…”

mentioning

confidence: 99%

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

Marek¹,

Lyčka²,

Kolehmainen³

et al. 2007

COC

131

110

View full text Add to dashboard Cite

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“…As a part of our ongoing project on cycloaddition reaction of nonstabilised azomethine ylides, we desired to study in more details the previously reported reaction of azomethine ylides generated from isatin and L-proline with the very effective dipolarophile (E)-b-nitrostyrene [46][47][48][49][50][51][52]. During the study on these reactions we modified the reaction in terms of better yield and short time ( Table 2).…”

Section: Resultsmentioning

confidence: 99%

“…The stereochemistry of cycloadduct type 6 is well known [45][46][47][48][49][50] but the stereochemistry of cycloadduct type 7 was established from the single crystal XRD study. Cycloadduct 7a was purified and crystallised in single crystal.…”

Section: Resultsmentioning

confidence: 99%

Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies

Gayen

Banerji

2014

Monatsh Chem

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Simple and efficient strategies towards the synthesis of substituted spiro-oxindole and oxazolidine systems by one-pot multi-component catalyst-free reactions utilising aryl aldehydes and a-amino acids have been developed. Owing to their complicated structure and ring strain spiro-oxindole moieties are not easily synthesised. In either route 1,3-dipolar cycloadditions involving non-stabilised azomethine ylides as intermediates, generated in situ from amino acids and aldehydes, with the dipolarophile present in the reaction mixture viz. (E)-bnitrostyrene, were utilised. The route to substituted oxazolidines involved cycloaddition to the C=O bond of a second molecule of the aldehyde.

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Potent Synergy between Spirocyclic Pyrrolidinoindolinones and Fluconazole against Candida albicans

et al. 2015

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A spiroindolinone (1S,3R,3aR,6aS)-1-benzyl-6′-chloro-5-(4-fluorophenyl)-7′-methylspiro[1,2,3a,6a-tetrahydropyrrolo[3,4-c]pyrrole-3,3′-1H-indole]-2′,4,6-trione was previously reported to enhance the antifungal effect of fluconazole against C. albicans. A diastereomer of that compound was synthesized, along with various analogues. Many of the compounds were shown to enhance the antifungal effect of fluconazole against C. albicans, some with exquisite potency. One spirocyclic piperazine derivative, which we have named synazo-1, enhanced the effect of fluconazole with EC50 of 300 pM against a susceptible strain of C. albicans and as low as 2 nM against some resistant strains. Synazo-1 exhibits true synergy with fluconazole with an FIC index below 0.5 in the strains tested. Synazo-1 exhibited low toxicity in mammalian cells relative to the concentrations required for the antifungal synergy.

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1H, 13C, 15N NMR, ESI mass spectral and single crystal X-ray structural characterization of three spiro[pyrrolidine-2,3′-oxindoles]

Cited by 6 publications

References 8 publications

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies

Potent Synergy between Spirocyclic Pyrrolidinoindolinones and Fluconazole against Candida albicans

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