Gold-catalyzed cyclization of unconjugated ynone derivatives for 2H-1,2-oxazine and 1-hydroxypyrrole skeletons through one-pot and single-step strategy

Taşdemir, Volkan; Menges, Nurettin

doi:10.1007/s11696-023-03041-6

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2024

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“…Gold catalyst can form C−C bonds, insert into C−H bonds and have properties such as reduction/oxidation [34] . If the nucleophilic atom attacks the inner carbon atom, exo‐dig closure will occur, and if it attacks the outer carbon atom, endo‐dig closure will occur [24,35–37] . The mechanism of the reaction appears to be the same as that proposed for gold‐catalyzed alkyne cyclization (Figure 2).…”

Section: Resultsmentioning

confidence: 79%

Synthesis of N‐ureido Pyrrole Derivatives Through Gold‐Catalysed Reaction: Solvent and Catalyst Effect

Taşdemir

2024

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Substituted pyrroles were obtained as a result of metal‐catalyzed cyclization of α propargyl acetophenone and α‐propargyl‐β‐ketoesters with semicarbazide. Optimum conditions and general procedures with high yields were established in a single pot. Eleven different N‐ureido‐pyrrole derivatives were successfully yielded. Different ynone derivatives having various functionalities did not affect the cyclization reaction but except a slight decrease in product yield. Screening of optimum catalyst revealed that gold(III) chloride was the best catalyst for the cyclization reaction. We believe that this is the first time an N‐ureido‐pyrrole skeleton starting from ynone has been synthesized in the literature.

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Section: Resultsmentioning

confidence: 79%