Green and Efficient Construction of Chromeno[3,4-c]pyrrole Core via Barton–Zard Reaction from 3-Nitro-2H-chromenes and Ethyl Isocyanoacetate

Green and Efficient Construction of Chromeno[3,4-c]pyrrole Core via Barton–Zard Reaction from 3-Nitro-2H-chromenes and Ethyl Isocyanoacetate

A regioselective one-pot method for the synthesis of 1-ethyl 2,4-dihydrochromene[3,4-c]pyrroles in 63–94% yields from available 2-phenyl-, 2-trifluoro(trichloro)methyl- or 2-phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes and ethyl isocyanoacetate through the Barton–Zard reaction in ethanol at reflu...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2022-12, Vol.27 (23), p.8456
Hauptverfasser: Kochnev, Ivan A., Barkov, Alexey Y., Zimnitskiy, Nikolay S., Korotaev, Vladislav Y., Sosnovskikh, Vyacheslav Y.
Format: Artikel
Sprache:eng
Schlagworte:
2,4-dihydrochromeno[3,4-c]pyrroles
3-nitro-2H-chromenes
Barton–Zard reaction
Ethanol
ethyl isocyanoacetate
Methods
Potassium carbonate
Pyrroles
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Zusammenfassung:A regioselective one-pot method for the synthesis of 1-ethyl 2,4-dihydrochromene[3,4-c]pyrroles in 63–94% yields from available 2-phenyl-, 2-trifluoro(trichloro)methyl- or 2-phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes and ethyl isocyanoacetate through the Barton–Zard reaction in ethanol at reflux for 0.5 h, using K2CO3 as a base, has been developed.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27238456