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GROUP-ASSISTED PURIFICATION CHEMISTRY PRINCIPLES TO ACCESS HIGHLY SUBSTITUTED ZWITTERIONIC FURANS via FAST, CONCISE, AND EFFICIENT ONE-POT THREE-COMPONENT ASSEMBLY

Abdolali Alizadeh, Reza Rezaiyehraad
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Abstract


Novel highly substituted zwitterionic furans were generated through the in situ formation of phosphonium salts. Firstly, intermediate salts were obtained via nucleophilic attack of Huisgen zwitterion to 3-cyanochromones. Finally, these intermediate salts underwent a proton migration, intramolecular cyclization, and ring-opening reaction to convert to the target products. The synthesized furans could be easily purified without traditional purification techniques (chromatography and recrystallization).


Keywords


3-cyanochromones; dialkyl acetylenedicarboxylate; triphenylphosphine; zwitterionic furans; one-pot reaction; three-component reaction.

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Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv