publication . Article . 2016

Protected diazonium salts: A continuous-flow preparation of triazenes including the anticancer compounds dacarbazine and mitozolomide

Christiane Schotten; Abdul Hadi Aldmairi; Yerbol Sagatov; Martyn Shepherd; Duncan L. Browne;
Open Access
  • Published: 01 Sep 2016 Journal: Journal of Flow Chemistry, volume 6, pages 218-225 (issn: 2062-249X, eissn: 2063-0212, Copyright policy)
  • Publisher: Springer Nature
  • Country: United Kingdom
Abstract
Herein, we report a continuous-flow process for the preparation of triazenes, whereby diazonium salts are generated and converted into their masked or protected triazene derivatives. Key to realizing the process, which is applicable to a wide range of substrates, is the identification of solvent and reagent parameters that avoid fouling and clogging in the tubing used in these studies. The process has also been applied to prepare the antineoplastic agents mitozolomide and dacarbazine. We also report isolation and differential scanning calorimetry (DSC) analysis of an anthranilic acidderived triazene whose related diazonium salt is a contact explosive. The data h...
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Subjects
free text keywords: Organic Chemistry, Chemistry (miscellaneous), Fluid Flow and Transfer Processes, QD, Triazene, chemistry.chemical_compound, chemistry, Green chemistry, Differential scanning calorimetry, Solvent, High-performance liquid chromatography, Reagent, Fouling, Exothermic process
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