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Sustainable synthesis routes towards urazole compounds

Laetitia Vlaminck (UGent) , Babs Van de Voorde (UGent) and Filip Du Prez (UGent)
(2017) GREEN CHEMISTRY. 19(23). p.5659-5664
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Abstract
Sustainable synthesis routes towards urazoles, the precursor molecules for triazolinediones, are reported. Not only is the use of isocyanates avoided, but the applied synthetic procedures are also mostly solventfree, high yielding and performed in an equimolar manner. Two complementary synthesis routes have been developed starting from a wide range of amines, both based on the use of diphenyl carbonate. The first method, which is particularly suitable for the synthesis of bulk urazoles, such as butyl, cyclohexyl or benzyl urazole, is performed in bulk in a one-pot fashion and generally results in yields between 87% and 96%. The second synthesis route, with yields up to 95%, focusses on the implementation of functionalities in the urazole structure and offers the possibility to generate bifunctional urazole compounds.
Keywords
TRIAZOLINEDIONE CLICK CHEMISTRY, THERMOPLASTIC ELASTOMERS, DIPHENYL, CARBONATE, TYROSINE, BIOCONJUGATION, ULTRAFAST, POLYMERS

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Citation

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Chicago
Vlaminck, Laetitia, Babs Van de Voorde, and Filip Du Prez. 2017. “Sustainable Synthesis Routes Towards Urazole Compounds.” Green Chemistry 19 (23): 5659–5664.
APA
Vlaminck, Laetitia, Van de Voorde, B., & Du Prez, F. (2017). Sustainable synthesis routes towards urazole compounds. GREEN CHEMISTRY, 19(23), 5659–5664.
Vancouver
1.
Vlaminck L, Van de Voorde B, Du Prez F. Sustainable synthesis routes towards urazole compounds. GREEN CHEMISTRY. 2017;19(23):5659–64.
MLA
Vlaminck, Laetitia, Babs Van de Voorde, and Filip Du Prez. “Sustainable Synthesis Routes Towards Urazole Compounds.” GREEN CHEMISTRY 19.23 (2017): 5659–5664. Print.
@article{8547583,
  abstract     = {Sustainable synthesis routes towards urazoles, the precursor molecules for triazolinediones, are reported. Not only is the use of isocyanates avoided, but the applied synthetic procedures are also mostly solventfree, high yielding and performed in an equimolar manner. Two complementary synthesis routes have been developed starting from a wide range of amines, both based on the use of diphenyl carbonate. The first method, which is particularly suitable for the synthesis of bulk urazoles, such as butyl, cyclohexyl or benzyl urazole, is performed in bulk in a one-pot fashion and generally results in yields between 87% and 96%. The second synthesis route, with yields up to 95%, focusses on the implementation of functionalities in the urazole structure and offers the possibility to generate bifunctional urazole compounds.},
  author       = {Vlaminck, Laetitia and Van de Voorde, Babs and Du Prez, Filip},
  issn         = {1463-9262},
  journal      = {GREEN CHEMISTRY},
  keywords     = {TRIAZOLINEDIONE CLICK CHEMISTRY,THERMOPLASTIC ELASTOMERS,DIPHENYL,CARBONATE,TYROSINE,BIOCONJUGATION,ULTRAFAST,POLYMERS},
  language     = {eng},
  number       = {23},
  pages        = {5659--5664},
  title        = {Sustainable synthesis routes towards urazole compounds},
  url          = {http://dx.doi.org/10.1039/c7gc02027a},
  volume       = {19},
  year         = {2017},
}

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