We report herein a general and efficient continuous flow‐based protocol for synthesizing thiophene‐2‐carboxylates starting from ketal‐functionalized β‐nitroacrylates. The protocol involves (i) a promoter‐free conjugate addition of thioacetic acid to β‐nitroacrylates, (ii) a base‐induced elimination of nitrous acid, and (iii) a final acid‐promoted domino cyclization‐aromatization process to afford the title targets. Thanks to the means of the flow chemistry and the use of solid supported systems, the three steps were combined in a whole flow chemical process, by which the products were isolated in good to excellent overall yields (38–88%).
β‐Nitroacrylates as Starting Materials of Thiophene‐2‐Carboxylates Under Continuous Flow Conditions
Chiurchiù, Elena;Gabrielli, Serena;Ballini, Roberto;Palmieri, Alessandro
2019-01-01
Abstract
We report herein a general and efficient continuous flow‐based protocol for synthesizing thiophene‐2‐carboxylates starting from ketal‐functionalized β‐nitroacrylates. The protocol involves (i) a promoter‐free conjugate addition of thioacetic acid to β‐nitroacrylates, (ii) a base‐induced elimination of nitrous acid, and (iii) a final acid‐promoted domino cyclization‐aromatization process to afford the title targets. Thanks to the means of the flow chemistry and the use of solid supported systems, the three steps were combined in a whole flow chemical process, by which the products were isolated in good to excellent overall yields (38–88%).File | Dimensione | Formato | |
---|---|---|---|
Adv. Synth.Catal.2019,361, 2042–2047.pdf
solo gestori di archivio
Descrizione: Adv. Synth.Catal.2019,361, 2042–2047
Tipologia:
Versione Editoriale
Licenza:
NON PUBBLICO - Accesso privato/ristretto
Dimensione
2 MB
Formato
Adobe PDF
|
2 MB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.