Synthesis and biological activity of 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxyhexitols

Kuszmann, J.; Medgyes, Gábor

doi:10.1016/s0008-6215(00)84675-3

Cited by 23 publications

(12 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…and crystallized from ethanol. Colourless crystals, m. p. ' H NMR (C6D6): 6 = 3,25 (dd; 2H; HIa = Has), 3,70 (dd; 2H; HIb = H6b), 4,83 (dd; 2H; H2 = H5), 4,51 (s; 2H; H3 = H4), 1,80 (s; 6H, GH4-CB3), 6,65 and 7,61 (each mc; 8H, (14): 1,46 g (10 mmol) of 6, dissolved in 10 ml of anhydrous pyridine, was treated at 0 "C with 2,53 g (22 mmol) of methylsulfonyl chloride, as described for 7. Following a similar work-up the material was crystallized As first fraction compound 9 was obtained; yield: 84 mg (1 1070 General procedure for hydrogenolysis of diazides and isolation of diamino dihydrochlorides: 1,0 mmol of diazide dissolved in 20 ml of methanol and 10 mg of 10% palladium on charcoal were vigorously stirred for 12 h at room temperature in a hydrogen atmosphere.…”

Section: 4:36-dianhydro-25-di-o-p-tolylsulfonyl-~-sorbitol(7)mentioning

confidence: 99%

Synthesis and properties of polyurethanes derived from diaminodianhydroalditols

Thiem

Lüders

1986

Makromol. Chem.

View full text Add to dashboard Cite

The readily accessible 1,4:3,6-dianhydroalditoIs with D-gluco-(l), L-ido-(5) and D-mannoconfigurations (6) were efficiently transformed into the 2,5-diamino-l,4:3,6-dianhydro-2,5-dideoxyalditols with D-gluco-(lo), D-manno-(13), and L-ido-configuration (16). Interfacial polycondensation of these chiral heterocyclic diamines as well as ethylene-and tetramethylene diamine with the bis(ch1oroformate) 3 derived from 1,4:3,6-dianhydro-~-sorbitol ga? the polyurethanes 17 to 21. Their number-average molecular weights were determined to be M , = 3 OOO corresponding to an average degree of polymerisation P, = 20. Inherent viscosities were measured, and H NMR spectroscopy as well as DSC gave informations about the molecular structure and some polymer properties.

show abstract

Section: 4:36-dianhydro-25-di-o-p-tolylsulfonyl-~-sorbitol(7)mentioning

confidence: 99%

Synthesis and properties of polyurethanes derived from diaminodianhydroalditols

Thiem

Lüders

1986

Makromol. Chem.

View full text Add to dashboard Cite

show abstract

“…Isosorbide bisazide was synthesized using the reported procedure . To a stirred solution of isosorbide bistosylate (2.0 g, 4.4 mmol) and anhydrous dimethylformamide (20 mL) in a round-bottom flask at room temperature, sodium azide (1.1 g, 17.6 mmol) was added in a portionwise manner.…”

Section: Methodsmentioning

confidence: 99%

“…Isosorbide bisazide was synthesized using the reported procedure. 50 To a stirred solution of isosorbide bistosylate (2.0 g, 4.4 mmol) and anhydrous dimethylformamide (20 mL) in a round-bottom flask at room temperature, sodium azide (1.1 g, 17.6 mmol) was added in a portionwise manner. Upon complete addition of sodium azide, the temperature of the reaction was increased to 140 °C and the mixture was stirred for 8 h. The reaction was monitored using TLC and continued till the consumption of bistosylate was noticed.…”

Section: Synthesis Of Isosorbide Bistosylatementioning

confidence: 99%

Understanding the Stereochemical Effect on the Properties of Emerging Thermosets: Sustainable Polybenzoxazines

Amarnath

Mukherjee

Lochab

2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Exploration of the properties of monomers by modulating their stereochemistry is not well reported in polybenzoxazines (PBzs). Isosorbide contains a rigid bicyclic (endo–exo-configuration) core that has shown promise in high-performance thermoplastic polymers. In this report, new chiral PBzs were prepared from industrially available feedstocks, carbohydrate-derived (isosorbide), and lignin- or cashew nut waste-sourced renewable phenols (cardanol and guaiacol). A fully biobased benzoxazine monomer based on a one-step condensation reaction of isosorbide diamine (isa) with phenols was carried out for 15 min under microwave and solvent- and catalyst-free conditions. Structural elucidation of monomers was achieved by two-dimensional (2D) NMR spectroscopy [heteronuclear single quantum correlation (HSQC) and COSY (correlated spectroscopy)]. The “isa”-based monomer revealed a comparable ring-opening polymerization temperature and a good processing window for the widely available bisphenol-A/aniline-based monomer. The resultant polymers showed a higher T g, better thermomechanical properties, and adhesive strength compared to other classical petrobased PBzs. The current work extends the importance of the major component of the sugar-derived isohexide family member, isosorbide, in polybenzoxazine chemistry and suggests that stereocontrol in the monomer is another approach to affect the thermomechanical properties of this upcoming class of high-performance phenolic polymer.

show abstract

“…106.5–108.5 °C (lit. 8a m.p. 101–102 °C); 1 H NMR (400 MHz, CDCl 3 ): δ =7.80–7.75 (m, 4 H), 7.36–7.32 (m, 4 H), 4.87–4.82 (m, 2 H), 4.59 (t, J =4.8 Hz, 1 H), 4.48 (d, J =4.5 Hz, 1 H), 3.92 (d, J =11.3 Hz, 1 H), 3.88–3.82 (m, 2 H), 3.66 (dd, J =9.8, 6.4 Hz, 1 H), 2.45 ppm (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): δ =145.3, 145.2, 132.9, 129.8, 127.7, 85.5, 83.2, 80.2, 78.2, 73.1, 69.7, 21.5 ppm; IR (neat): $\tilde \nu $ =1596, 1366, 1176, 1087, 1049, 967 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

Renewable Rigid Diamines: Efficient, Stereospecific Synthesis of High Purity Isohexide Diamines

et al. 2011

View full text Add to dashboard Cite

We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high-performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo-isomers, dideoxy-diamino isoidide and dideoxy-diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy-amino isomannide-a tricyclic adduct-was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics.

show abstract

Synthesis and biological activity of 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxyhexitols

Cited by 23 publications

References 12 publications

Synthesis and properties of polyurethanes derived from diaminodianhydroalditols

Synthesis and properties of polyurethanes derived from diaminodianhydroalditols

Understanding the Stereochemical Effect on the Properties of Emerging Thermosets: Sustainable Polybenzoxazines

Renewable Rigid Diamines: Efficient, Stereospecific Synthesis of High Purity Isohexide Diamines

Contact Info

Product

Resources

About