4-(1-Haloalkyl)-3-nitrotetrahydrofurans as versatile scaffolds for the synthesis of diversely functionalized tetrahydrofurans

Jahn, Ullrich; Rudakov, Dmytro; Jones, Peter G.

doi:10.1016/j.tet.2011.11.023

Cited by 8 publications

(1 citation statement)

References 36 publications

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“…H-bond interactions between NH of the carbamate groups and ether oxygens are rare in the literature. Linear one-dimensional chains showing this particular motif have been reported five times in the CCDC database to the best of our knowledge. − In addition, a literature search in the same database for H-bond interactions between tetracyclic ethers and amino groups resulted in only three hits, two of which were derivatives with a taxane backbone. − In taxanes in particular, these hydrogen bonds have so far been overlooked because in the crystal structures of the derivatives reported, these bonds have shown distances B(H)···A of above 3.00 Å, thus being considered too weak to have a large influence. The intermolecular interactions in DOW2Et are the shortest ones reported so far in the literature.…”

Section: Results and Discussionmentioning

confidence: 99%

The Devil is in the Detail: A Rare H-Bonding Motif in New Forms of Docetaxel

Vella‐Żarb

Dinnebiér

Baisch

2013

Crystal Growth & Design

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Docetaxel is a semisynthetic analog of the taxane paclitaxel, pivotal for the treatment of various types of cancer. Minor differences in its chemical structure give docetaxel a slightly better water solubility profile when compared to paclitaxel. An understanding of the hydrogenbonding network in docetaxel is therefore imperative if an explanation for its improved solubility over its predecessor is to be sought. New crystalline forms for solvated (ethanol), hydrated, and anhydrous docetaxel are reported. The crystal structures were determined by single crystal synchrotron and laboratory powder X-ray diffraction experiments on crystalline materials resulting from polymorph screening tests in various solvents. Variable-temperature experiments were carried out over ranges between 20 and 130 °C, with subsequent loss of crystal water at 70 and 90 °C. The resulting structures are discussed in terms of their intermolecular interactions, molecular conformations, and packing motifs. A rare hydrogen-bonding motif, observed between carbamate and tetracyclic ether groups, was found in the packing of all phases of docetaxel. Subtle but significant changes in structural hydrogen bonding motifs are discussed and their differences supported and visualized by Hirshfeld surface calculations and related two-dimensional fingerprint plots.

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Section: Results and Discussionmentioning

confidence: 99%

The Devil is in the Detail: A Rare H-Bonding Motif in New Forms of Docetaxel

Vella‐Żarb

Dinnebiér

Baisch

2013

Crystal Growth & Design

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Asymmetric Synthesis of Cyclohexane‐Fused Drug‐Like Spirocyclic Scaffolds Containing Six Contiguous Stereogenic Centers via Organocatalytic Cascade Reactions

et al. 2015

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Drug‐like spirocyclic scaffolds have been prepared asymmetrically by fusing fully functionalized cyclohexanes with medicinally important pyrazolone, rhodanine, barbituric acid or indandione moieties. This approach utilizes an organocatalytic tandem Michael–Michael–aldol reaction that yields diverse chiral spirocyclic backbones containing six contiguous stereogenic centers and multiple functional groups. The target compounds are generated in good yield and with high stereoselectivity (up to 99 % ee and 95:5 dr). Intriguingly, diastereocontrol of the spiro‐products changes depending on the substrate.magnified image

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Copper(I)‐Catalyzed Synthesis of Chlorinated Tetrahydropyridazin‐3‐ones and 1,2‐Diazepan‐3‐ones from N‐Allyl‐N′‐trichloroacetylhydrazines

Ram

Soni

2016

Adv Synth Catal

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Thes ynthesis of chlorinatedt etrahydropyridazin-3-ones and 1,2-diazepan-3-ones hasb eend eveloped. Thep resentp aper describes the application of Cu(I)-catalyzed ATRC for the synthesis of heterocyclicm olecules containing two heteroatoms (i.e., nitrogen) in the ring for the first time.A ne asy separation of the individual compounds from the product mixture could be achieved by considering their solubility/insolubility in n-hexane. Thep resence of three chlorine atoms providesp ossibilitiesf or furtherd erivatization.

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4-(1-Haloalkyl)-3-nitrotetrahydrofurans as versatile scaffolds for the synthesis of diversely functionalized tetrahydrofurans

Cited by 8 publications

References 36 publications

The Devil is in the Detail: A Rare H-Bonding Motif in New Forms of Docetaxel

The Devil is in the Detail: A Rare H-Bonding Motif in New Forms of Docetaxel

Asymmetric Synthesis of Cyclohexane‐Fused Drug‐Like Spirocyclic Scaffolds Containing Six Contiguous Stereogenic Centers via Organocatalytic Cascade Reactions

Copper(I)‐Catalyzed Synthesis of Chlorinated Tetrahydropyridazin‐3‐ones and 1,2‐Diazepan‐3‐ones from N‐Allyl‐N′‐trichloroacetylhydrazines

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