Synthesis of 4‐Furan‐ and 4‐Pyrrol‐3‐yl‐2H‐chromenes from Naturally‐occurring Compounds by Gold(I)‐Catalyed Domino Reactions

A gold‐catalyzed cascade double cyclization reaction has been designed to synthesize heterobiaryl compounds such as furanyl and pyrrolyl 2H‐chromenes from bis(alkynyl)‐1,2‐diols and 1,2‐amino alcohols. The starting materials are readily available from biomass platform molecules such as α‐hydroxy aci...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-06, Vol.365 (12), p.2049-2056
Main Authors: Solas, Marta, Renedo, Lorena, Suárez‐Pantiga, Samuel, Sanz, Roberto
Format: Article
Language:English
Subjects:
Alcohols
Alkynes
Amino acids
annulation
Cascade chemical reactions
Chemical reactions
chromenes
Diols
furans
Gold
hydroarylation
Hydroxy acids
pyrroles
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Summary:A gold‐catalyzed cascade double cyclization reaction has been designed to synthesize heterobiaryl compounds such as furanyl and pyrrolyl 2H‐chromenes from bis(alkynyl)‐1,2‐diols and 1,2‐amino alcohols. The starting materials are readily available from biomass platform molecules such as α‐hydroxy acids and α‐amino acids. The process involves an initial heterocyclodehydration step enabling the formation of the furan or pyrrole ring, followed by an alkyne hydroarylation to form the chromene core.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300300