Synthesis and Some Spectral Characteristics of Bicyclic Phosphate, GABA Antagonists

Ozoe, Yoshihisa; Etō, Morifusa

doi:10.1080/00021369.1982.10865065

Cited by 3 publications

(4 citation statements)

References 3 publications

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“…Even though this procedure is often successful, yields are seriously lowered owing to the formation of formylated or partially hydroxylated byproducts, whose separation is not trivial 14d. A complementary route is malonic ester synthesis, in which dialkyl malonate is first alkylated to introduce the R group and then hydroxymethylated with formaldehyde 14e,f. The subsequent reduction step requires protection of the hydroxymethyl group and is usually carried out with LiAlH 4 under rather drastic conditions that narrow the synthetic scope of the method 14e.…”

Section: Resultsmentioning

confidence: 99%

“…A complementary route is malonic ester synthesis, in which dialkyl malonate is first alkylated to introduce the R group and then hydroxymethylated with formaldehyde 14e,f. The subsequent reduction step requires protection of the hydroxymethyl group and is usually carried out with LiAlH 4 under rather drastic conditions that narrow the synthetic scope of the method 14e. A similar procedure entails alkylation of sodium triethyl methane tricarboxylate14g followed by reduction, which can interfere with other functional groups.…”

Section: Resultsmentioning

confidence: 99%

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Magnetostructural Correlations in Tetrairon(III) Single‐Molecule Magnets

Gregoli

Danieli

Barra

et al. 2009

Chemistry A European J

117

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Tunable single-molecule magnets: The spin-level landscape in a series of Fe(III) (4) single-molecule magnets with propeller-like structure was analyzed by means of high-frequency EPR spectroscopy. The zero-field splitting parameter D of the ground S=5 spin state correlates strongly with the pitch of the propeller gamma (see picture), and thus provides a simple link between molecular structure and magnetic behavior.We report three novel tetrairon(III) single-molecule magnets with formula [Fe(4)(L)(2)(dpm)(6)] (Hdpm=2,2,6,6-tetramethylheptane-3,5-dione), prepared by using pentaerythritol monoether ligands H(3)L=R'OCH(2)C(CH(2)OH)(3) with R'=allyl (1), (R,S)-2-methyl-1-butyl (2), and (S)-2-methyl-1-butyl (3), along with a new crystal phase of the complex containing H(3)L=11-(acetylthio)-2,2-bis(hydroxymethyl)- undecan-1-ol (4). High-frequency EPR (HF-EPR) spectra at low temperature were collected on powder samples in order to determine the zero-field splitting (zfs) parameters in the ground S=5 spin state. In 1-4 and in other eight isostructural compounds previously reported, a remarkable correlation is found between the axial zfs parameter D and the pitch gamma of the propeller-like structure. The relationship is directly demonstrated by 1, which features both structurally and magnetically inequivalent molecules in the crystal. The dynamics of magnetization has been investigated by ac susceptometry, and the results analyzed by master-matrix calculations. The large rhombicities of 2 and 3 were found to be responsible for the fast magnetic relaxation observed in the two compounds. However, complex 3 shows an additional faster relaxation mechanism which is unaccounted for by the set of spin Hamiltonian parameters determined by HF-EPR.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Magnetostructural Correlations in Tetrairon(III) Single‐Molecule Magnets

Gregoli

Danieli

Barra

et al. 2009

Chemistry A European J

117

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“…The 5‐(hydroxymethyl)‐2,2‐dioxo[1,3,2]dioxathian‐5‐ol ( 7 ) is a formal derivative of 2‐(hydroxymethyl)propane‐1,2,3‐triol, also called isoerythritol 22. Derivatives of isoerythritol have come to prominent attention as acyclic nucleoside analogues23 and as GABA analogues 24. With use of the formal isoerythritol derivative 11 , each of the primary hydroxy functions of isoerythritol may selectively be addressed.…”

Section: Resultsmentioning

confidence: 99%

Easy Access to Derivatives of 2‐(Hydroxymethyl)propane‐1,2,3‐triol (Isoerythritol) with up to Four Separately Addressable Functionalities

et al. 2003

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5‐Methylene‐2‐oxo[1,3,2]dioxathiane (2) was obtained in 91% yield from 2‐methylenepropane‐1,3‐diol (1) and thionyl chloride. The cyclic sulfite 2 reacts with a variety of nucleophiles to give formally monosubstituted products 3 of the diol 1 in 62−77% yield. Oxidation of 2 with RuCl3/NaIO4 yields the diprotected tetraol 5‐(hydroxymethyl)‐2,2‐dioxo[1,3,2]dioxathian‐5‐ol (7) in 86% yield, which can be used to easily access tetrafunctional derivatives of 2‐(hydroxymethyl)propane‐1,2,3‐triol (isoerythritol); for example, acetylation with acetic anhydride furnishes in 96% yield the primary acetate 11, which reacts with potassium cyanide and sodium azide to give the 2‐cyano‐ and 2‐(azidomethyl)propane‐1,2,3‐triol monoacetates 12a,b (78 and 82% yield, respectively). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…6 ) Absorption spectra were recorded on a Hitachi Model 200-20 spectrophotometer. For kinetic studies, the cuvettes were maintained at a constant temperature with a Komatsu-Yamato CTR-120 Coolnics circulator.…”

Section: Methodsmentioning

confidence: 99%