The electrochemical reduction of caffeine, never carried out previously, yielded in DMF-Et 4 NBF 4 N -formyl- N,1-dimethyl-4-(methylamino)-1 H -imidazole-5-carboxamide, a highly functionalized imidazole product derived from the opening of the uracil ring. This reactivity is different from that of the methylated salt of caffeine, the cathodic reduction of which leads to the opening of the imidazole ring. Moreover, the product obtained by cathodic reduction, formylated at the exocyclic amide nitrogen, is different from that formed by treatment in an aqueous solution of sodium hydroxide followed by formylation. The latter is formylated at the exocyclic amine nitrogen.

Cathodic reduction of caffeine: synthesis of an amino-functionalized imidazole from a biobased reagent / Pandolfi, F.; Chiarotto, I.; Mattiello, L.; Rocco, D.; Feroci, M.. - In: SYNLETT. - ISSN 0936-5214. - 30:10(2019), pp. 1215-1218. [10.1055/s-0037-1611483]

Cathodic reduction of caffeine: synthesis of an amino-functionalized imidazole from a biobased reagent

Pandolfi F.
Membro del Collaboration Group
;
Chiarotto I.
Membro del Collaboration Group
;
Mattiello L.
Membro del Collaboration Group
;
Rocco D.
Membro del Collaboration Group
;
Feroci M.
Membro del Collaboration Group
2019

Abstract

The electrochemical reduction of caffeine, never carried out previously, yielded in DMF-Et 4 NBF 4 N -formyl- N,1-dimethyl-4-(methylamino)-1 H -imidazole-5-carboxamide, a highly functionalized imidazole product derived from the opening of the uracil ring. This reactivity is different from that of the methylated salt of caffeine, the cathodic reduction of which leads to the opening of the imidazole ring. Moreover, the product obtained by cathodic reduction, formylated at the exocyclic amide nitrogen, is different from that formed by treatment in an aqueous solution of sodium hydroxide followed by formylation. The latter is formylated at the exocyclic amine nitrogen.
File allegati a questo prodotto
File Dimensione Formato  
Pandolfi_Cathodic Reduction_postprint_2019.pdf

embargo fino al 01/10/2020

Tipologia: Documento in Post-print (versione successiva alla peer review e accettata per la pubblicazione)
Licenza: Tutti i diritti riservati (All rights reserved)
Dimensione 147.58 kB
Formato Adobe PDF
147.58 kB Adobe PDF Visualizza/Apri PDF
Pandolfi_Cathodic_2019.pdf

solo gestori archivio

Tipologia: Versione editoriale (versione pubblicata con il layout dell'editore)
Licenza: Tutti i diritti riservati (All rights reserved)
Dimensione 684.66 kB
Formato Adobe PDF
684.66 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/1281872
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 6
social impact