Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives

doi:10.3390/91100922

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Molecules 2004, 9(11), 922-938; doi:10.3390/91100922

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Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives

Nurettin Sadikov¹, Sahin Nasibov¹, Cemil Ogretir^2,* , Halil Berber³ and Ali Hüseyinli⁴

¹ Baku St. University, Faculty of Chemistry, Department of Organic Chemistry, Baku, Azerbaijan ² Osmangazi University, Faculty of Arts and Sciences, Chemistry Department, 26040 Eskişehir, Turkey ³ Anadolu University, Faculty of Sciences, Chemistry Department, 26470 Eskişehir, Turkey ⁴ Baku St. University, Faculty of Chemistry, Department of Analytical Chemistry, Baku, Azerbaijan

* Author to whom correspondence should be addressed.

Received: 5 March 2004 / Accepted: 24 June 2004 / Published: 30 November 2004

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Abstract: The alkylation of β-dicarbonyl compounds in a K₂CO₃/DMSO system wasfound to afford O- and C-alkylated derivatives, depending on the type of the β-dicarbonylcompound involved. The alkyl derivatives obtained were used in the synthesis of some newspiro barbituric acid derivatives. Quantum chemical calculations were carried out toelucidate the reaction mechanisms for some typical synthesis.

Keywords: Alkylation of β-dicarbonyl compounds; spiro derivatives of barbituric acid; 2-chloro-1-(2- chloroethoxy)ethane; theoretical studies.

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MDPI and ACS Style

Sadikov, N.; Nasibov, S.; Ogretir, C.; Berber, H.; Hüseyinli, A. Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives. Molecules 2004, 9, 922-938.

AMA Style

Sadikov N, Nasibov S, Ogretir C, Berber H, Hüseyinli A. Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives. Molecules. 2004; 9(11):922-938.

Chicago/Turabian Style

Sadikov, Nurettin; Nasibov, Sahin; Ogretir, Cemil; Berber, Halil; Hüseyinli, Ali. 2004. "Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives." Molecules 9, no. 11: 922-938.

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