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Journals / Turkish Journal of Chemistry / 2008 / Cilt: 32 - Sayı: 4

Oxidative Cyclisation of 3-Oxopropanenitriles Mediated Manganese(III) Acetate with 2-Thienyl Substituted Alkenes

Mehmet YILMAZ
Neşe UZUNALİOĞLU
Mehtap YAKUT
A. Tarık PEKEL
Pages
411–422
Publication Date
2008-04-01
DOI
—
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AI Summary & Key Takeaways

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⚡ TL;DR(Too Long; Didn't Read)

In addition, the reactions of 2-(1-phenylvinyl)thiophene 2c with various 3-oxopropanenitriles produced 4,5-dihydrofurans 3j-n containing heterocycle in 77%-91% yields.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:The oxidative cyclisation of 3-oxopropanenitriles 1a-g with alkenes 2a-c containing 2-thienyl group by manganese(III) acetate was studied.
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Key Findings & Data:Treatment of 3-oxopropanenitriles 1a-d with 2-[(E)-2-phenylvinyl] thiophene 2a gave 4-phenyl-5-(2-thienyl)-4,5-dihydrofuran-3-carbonitriles 3a-d in moderate yields (52%-60%). 5-(2-thienyl) substituted 4,5-dihydrofuran-3-carbonitriles 3e-i were obtained by the oxidative cyclisation of these 3-oxopropanenitriles with 2-[(E)-1-methyl-2- phenylvinyl]thiophene 2b in good yields (54%-68%).
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Conclusion & Impact:In addition, the reactions of 2-(1-phenylvinyl)thiophene 2c with various 3-oxopropanenitriles produced 4,5-dihydrofurans 3j-n containing heterocycle in 77%-91% yields.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Manganese(III) acetate · oxidative cyclisation · 5-dihydrofuran-3-carbonitrile

Abstract

The oxidative cyclisation of 3-oxopropanenitriles 1a-g with alkenes 2a-c containing 2-thienyl group by manganese(III) acetate was studied. Treatment of 3-oxopropanenitriles 1a-d with 2-[(E)-2-phenylvinyl] thiophene 2a gave 4-phenyl-5-(2-thienyl)-4,5-dihydrofuran-3-carbonitriles 3a-d in moderate yields (52%-60%). 5-(2-thienyl) substituted 4,5-dihydrofuran-3-carbonitriles 3e-i were obtained by the oxidative cyclisation of these 3-oxopropanenitriles with 2-[(E)-1-methyl-2- phenylvinyl]thiophene 2b in good yields (54%-68%). In addition, the reactions of 2-(1-phenylvinyl)thiophene 2c with various 3-oxopropanenitriles produced 4,5-dihydrofurans 3j-n containing heterocycle in 77%-91% yields.

Özet

The oxidative cyclisation of 3-oxopropanenitriles 1a-g with alkenes 2a-c containing 2-thienyl group by manganese(III) acetate was studied. Treatment of 3-oxopropanenitriles 1a-d with 2-[(E)-2-phenylvinyl] thiophene 2a gave 4-phenyl-5-(2-thienyl)-4,5-dihydrofuran-3-carbonitriles 3a-d in moderate yields (52%-60%). 5-(2-thienyl) substituted 4,5-dihydrofuran-3-carbonitriles 3e-i were obtained by the oxidative cyclisation of these 3-oxopropanenitriles with 2-[(E)-1-methyl-2- phenylvinyl]thiophene 2b in good yields (54%-68%). In addition, the reactions of 2-(1-phenylvinyl)thiophene 2c with various 3-oxopropanenitriles produced 4,5-dihydrofurans 3j-n containing heterocycle in 77%-91% yields.

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Cite This Article

YILMAZ, M., UZUNALİOĞLU, N., YAKUT, M., PEKEL, A. T. (2008). Oxidative Cyclisation of 3-Oxopropanenitriles Mediated Manganese(III) Acetate with 2-Thienyl Substituted Alkenes. Turkish Journal of Chemistry, Cilt: 32 - Sayı: 4, 411–422. https://ajindex.com/articles/185045

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