Isocyanates of heterocyclic compounds. I. The Synthesis of 2,5‐Diisocyanatofuran

Nielek, Stefan; Lesiak, T.

doi:10.1002/prac.19883300523

Cited by 21 publications

(26 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[38,58] Although a few scattered reports on double Curtius rearrangements onto α-positions of fivemembered heterocycles exist in the literature, [59][60][61][62] use of this strategy to prepare 2,5-disubstituted bisamides has not yet been reported. [38,58] Although a few scattered reports on double Curtius rearrangements onto α-positions of fivemembered heterocycles exist in the literature, [59][60][61][62] use of this strategy to prepare 2,5-disubstituted bisamides has not yet been reported.…”

Section: Thiophene Derivativesmentioning

confidence: 99%

2,5‐Diamide‐Substituted Five‐Membered Heterocycles: Challenging Molecular Synthons

Fabbro¹,

Armani²,

Carloni³

et al. 2014

Eur J Org Chem

View full text Add to dashboard Cite

We describe synthetic routes for preparing previously unknown 2,5‐diamide‐substituted five‐membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius‐like rearrangement reactions. Conformation analysis of the 2,5‐diamidothiophene derivatives identified a “closed” conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.

show abstract

Section: Thiophene Derivativesmentioning

confidence: 99%

2,5‐Diamide‐Substituted Five‐Membered Heterocycles: Challenging Molecular Synthons

Fabbro¹,

Armani²,

Carloni³

et al. 2014

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…The furan ester 7 was synthesized according to literature methods. [10,11] Chloromethylation of commercially available methyl furan-2-carboxylate (6) with paraformaldehyde, zinc chloride and anhydrous hydrogen chlo-ride yielded 7. The chloro substituent was replaced according to a literature procedure [12,13] to obtain 8 by heating 7 with anhydrous sodium acetate in acetic acid containing acetic anhydride.…”

Section: Resultsmentioning

confidence: 99%

2‐(Guanidiniocarbonyl)furans as a New Class of Potential Anion Hosts: Synthesis and First Binding Studies

Schmuck

Machon

2006

Eur J Org Chem

View full text Add to dashboard Cite

The synthesis of a new class of potential anion hosts, the 2‐(guanidiniocarbonyl)furans 5a–d, is presented in this study. The facile decomposition of furans under acidic conditions makes the synthesis of these compounds challenging. First binding studies showed that the (guanidiniocarbonyl)furans are much more acidic (pKa ≈ 5.5) than the analogous pyrroles (pKa ≈ 7) previously introduced by us for oxoanion binding in aqueous solvents. Hence, anion binding with the furan derivatives occurs only in acidic solutions below pH = 5. Therefore, carboxylates are not bound efficiently, whereas, for example, the less basic hydrogen sulfate is bound by 5b with an association constant of K = 600 M–1 in aqueous DMSO even in the presence of a large excess of buffer. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

show abstract

“…E.g., 2,5-bis(aminomethyl)furan can be synthesized from DFF as reported by El Hajj et al [70] while 2,5-diisocyanatofuran is derived from FDC by reaction with sodium azide. [71] The above mentioned side reaction occurring during the acid catalyzed synthesis of HMF from cellulose and cellulose-derived sugars by re-hydration of HMF yields levulinic acid (LA) and one equivalent of formic acid. LA poses another platform chemical of high importance ( Figure 9).…”

Section: -Hydroxymethylfurfural and Levulinic Acidmentioning

confidence: 99%

Cellulose‐Based Sustainable Polymers: State of the Art and Future Trends

Rose

Palkovits

2011

Macromol. Rapid Commun.

169

141

View full text Add to dashboard Cite

Nowadays, nearly all polymeric materials are produced from crude oil-derived monomers. With the steadily increasing demand for oil-based products and their decreasing availability in the near future, one of the main challenges of mankind is the replacement of crude oil as raw material by renewable resources such as biomass. So far, only a few polymers are available derived directly from cellulose as a main component of biomass by regeneration. On the other hand, a significant potential lies in the production of polymers from cellulose-derived monomers. A huge variety of different monomers is already available by convenient catalytic processes. This feature article focuses on the current status of mono- and resulting polymers derived either directly from cellulose processing and regeneration or by catalytic conversion to a number of monomers for the production of novel polymers and co-polymers.

show abstract

Isocyanates of heterocyclic compounds. I. The Synthesis of 2,5‐Diisocyanatofuran

Cited by 21 publications

References 1 publication

2,5‐Diamide‐Substituted Five‐Membered Heterocycles: Challenging Molecular Synthons

2,5‐Diamide‐Substituted Five‐Membered Heterocycles: Challenging Molecular Synthons

2‐(Guanidiniocarbonyl)furans as a New Class of Potential Anion Hosts: Synthesis and First Binding Studies

Cellulose‐Based Sustainable Polymers: State of the Art and Future Trends

Contact Info

Product

Resources

About