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Protected Diazonium Salts: A Continuous-Flow Preparation of Triazenes Including the Anticancer Compounds Dacarbazine and Mitozolomide

Protected Diazonium Salts: A Continuous-Flow Preparation of Triazenes Including the Anticancer... 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 highlights improved stability but also suggests that an exothermic process does occur with an onset temperature of 118 °C. Finally, an 18-hour continuous operation of the reaction procedure using high-performance liquid chromatography (HPLC) pumps is reported. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Protected Diazonium Salts: A Continuous-Flow Preparation of Triazenes Including the Anticancer Compounds Dacarbazine and Mitozolomide

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Publisher
Springer Journals
Copyright
2016 Akadémiai Kiadó
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1556/1846.2016.00025
Publisher site
See Article on Publisher Site

Abstract

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 highlights improved stability but also suggests that an exothermic process does occur with an onset temperature of 118 °C. Finally, an 18-hour continuous operation of the reaction procedure using high-performance liquid chromatography (HPLC) pumps is reported.

Journal

Journal of Flow ChemistrySpringer Journals

Published: Jul 1, 2016

Keywords: chemistry/food science, general; green chemistry; organic chemistry; inorganic chemistry; nanochemistry; industrial chemistry/chemical engineering

References