Journals / Turkish Journal of Chemistry / 2012 / Cilt: 36 - Sayı: 3

The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives

Pages
485–492
Publication Date
2012-03-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.

📌 3 Key Takeaways

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Objective & Hypothesis:A 3-component domino reaction approach between a primary amine, a dialkyl acetylenedicarboxylate, and 2-oxo-2- phenylacetaldehyde that affords novel alkyl 2-benzoyl-4-alkylamino- 5-oxo-2,5-dihydro-3-furan carboxylate derivatives is reported.
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Key Findings & Data:The reaction sequence consists of an initial Michael addition of primary amines to dialkyl acetylenedicarboxylates, followed by an aldol-like reaction with 2-oxo-2-phenylacetaldehyde, and then g -lactonization to afford the products.
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Conclusion & Impact:This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Dialkyl acetylenedicarboxylates · 2-oxo-2-phenylacetaldehyde · primary amines

Abstract

A 3-component domino reaction approach between a primary amine, a dialkyl acetylenedicarboxylate, and 2-oxo-2- phenylacetaldehyde that affords novel alkyl 2-benzoyl-4-alkylamino- 5-oxo-2,5-dihydro-3-furan carboxylate derivatives is reported. The reaction sequence consists of an initial Michael addition of primary amines to dialkyl acetylenedicarboxylates, followed by an aldol-like reaction with 2-oxo-2-phenylacetaldehyde, and then g -lactonization to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.

Özet

A 3-component domino reaction approach between a primary amine, a dialkyl acetylenedicarboxylate, and 2-oxo-2- phenylacetaldehyde that affords novel alkyl 2-benzoyl-4-alkylamino- 5-oxo-2,5-dihydro-3-furan carboxylate derivatives is reported. The reaction sequence consists of an initial Michael addition of primary amines to dialkyl acetylenedicarboxylates, followed by an aldol-like reaction with 2-oxo-2-phenylacetaldehyde, and then g -lactonization to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.

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Cite This Article

SAFAEI-GHOMI, J., SALIMI, F., RAMAZANI, A. (2012). The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives. Turkish Journal of Chemistry, Cilt: 36 - Sayı: 3, 485–492. https://ajindex.com/articles/185235

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