Synthesis and Structure of New Macrocycles Including Spiro‐1,3‐Dioxane Units

Grosu, Ion; Bogdan, Elena; Plé, G.; Toupet, Loı̈c; Ramondenc, Yvan; Condamine, Eric; Peulon-Agasse, Valérie; Balog, Mirela

doi:10.1002/ejoc.200200615

Cited by 10 publications

(5 citation statements)

References 48 publications

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“…Spiran 3 was characterized by NMR spectroscopy and melting point was determined using a Boetius microscope. Both melting point [22] and NMR are in accordance with literature data.…”

Section: Resultssupporting

confidence: 90%

Research Article. Precursor Synthesis of Some New Macrocyclic Compounds

Gâz-Florea

Mircia

Berța

2017

Acta Medica Marisiensis

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Objective: Development of new electronic devices with applications in computer science as well as new medical devices pushed the researcher to find new technologies. Based on those new techniques we have designed and synthesized compounds with possible application in the field of advanced materials. Material and method: Compounds were analyzed by TLC and NMR. Routine 1H NMR (250 MHz) spectra were recorded at room temperature in deuterated acetone, unless stated otherwise. Thin-layer chromatography (TLC) was carried out on aluminum sheets coated with silicagel 60 F254 Merck TLC plates. Results: Starting from commercial available compounds intermediates were obtained in a good yield. 4,4'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)diphenol was obtained starting from pentaerythritol and p-hydroxy-benzaldehyde in the presence of catalytic amounts of APTS (p-toluensulfonic acid). The product was purified by recrystallization and characterized by NMR spectroscopy. The structure exhibit 2 different signals for equatorial and axial position. Furthermore di, tri and tetra ethylene glycol were obtained by microwave assisted synthesis in a matter of minutes. Compounds were separated by recrystallization. Conclusions: In conclusion, several intermediates were synthesized and characterized from spectroscopic point of view. Further analyses should be carried out and the compounds should be tested as advanced materials.

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“…Spiran 3 was characterized by NMR spectroscopy and melting point was determined using a Boetius microscope. Both melting point [22] and NMR are in accordance with literature data.…”

Section: Resultssupporting

confidence: 90%

Research Article. Precursor Synthesis of Some New Macrocyclic Compounds

Gâz-Florea

Mircia

Berța

2017

Acta Medica Marisiensis

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“…As examples, the X-ray structure of macrocycles exhibiting 2,4,8,10-tetraoxaspiro [5.5]undecane units monomer 87 [115] (Fig. ( 14)) and dimer 88 [116] (Fig.…”

Section: Monospiranesmentioning

confidence: 99%

Six-Membered Ring Spiranes: Carbocycles and Heterocycles with Oxygen

Cismas¹,

Terec²,

Mager³

et al. 2005

COC

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The data concerning the structure, synthesis and reactivity of six-membered ring spiranes exhibiting carbocycles and heterocycles with oxygen atoms are reviewed. The structural aspects are discussed using specific stereogenic elements and stereochemistry descriptors for spiranes with six-membered rings. The data are supported by high field NMR investigations and molecular structures obtained by X-ray diffractometry. The general procedures and access to spiranes with carbocycles and with heterocycles with oxygen are commented.

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“…While it is possible to synthesize both acyclic and cyclic acetals, spirocyclic conformation confers rigidity to the polymer backbone as a result of its restricted conformational flexibility and, hence, results in enhanced polymer thermal stability [ 30 , 31 , 32 ]. In this context, spirocyclic polyacetals with various chemical structures have been synthesized via different polymerization methods.…”

Section: Introductionmentioning

confidence: 99%

Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo

et al. 2021

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Polymeric nanomaterials that degrade in acidic environments have gained considerable attention in nanomedicine for intracellular drug delivery and cancer therapy. Among various acid-degradable linkages, spirocyclic acetals have rarely been used to fabricate such vehicles. In addition to acid sensitivity, they benefit from conformational rigidity that is otherwise not attainable by their non-spirocyclic analogs. Herein, amphiphilic spirocyclic polyacetals are synthesized by Cu-catalyzed alkyne–azide “click” polymerization. Unlike conventional block copolymers, which often form core–shell structures, these polymers self-assemble to form core amphiphilic assemblies capable of encapsulating Nile red as a hydrophobic model drug. In vitro experiments show that while release from these materials can occur at neutral pH with preservation of their integrity, acidic pH accelerates efficient cargo release and leads to the complete degradation of assemblies. Moreover, cellular assays reveal that these materials are fully cytocompatible, interact with the plasma membrane, and can be internalized by cells, rendering them as potential candidates for cancer therapy and/or drug delivery.

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Synthesis and Structure of New Macrocycles Including Spiro‐1,3‐Dioxane Units

Cited by 10 publications

References 48 publications

Research Article. Precursor Synthesis of Some New Macrocyclic Compounds

Research Article. Precursor Synthesis of Some New Macrocyclic Compounds

Six-Membered Ring Spiranes: Carbocycles and Heterocycles with Oxygen

Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo

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