Quantum chemical and experimental studies on the mechanism of alkylation of beta-dicarbonyl compounds. The synthesis of five and six membered heterocyclic spiro derivatives

Nurettin Sadikov; Sahin Nasibov; Cemil Oğretir; Halil Berber; Ali Hüseyinli

doi:10.3390/91100922

Quantum chemical and experimental studies on the mechanism of alkylation of beta-dicarbonyl compounds. The synthesis of five and six membered heterocyclic spiro derivatives

Molecules. 2004 Nov 30;9(11):922-38. doi: 10.3390/91100922.

Authors

Nurettin Sadikov¹, Sahin Nasibov, Cemil Oğretir, Halil Berber, Ali Hüseyinli

Affiliation

¹ Baku St. University, Faculty of Chemistry, Department of Organic Chemistry, Baku, Azerbayijan.

Abstract

The alkylation of beta-dicarbonyl compounds in a K2CO3/DMSO system was found to afford O- and C-alkylated derivatives, depending on the type of the beta-dicarbonyl compound involved. The alkyl derivatives obtained were used in the synthesis of some new spiro barbituric acid derivatives. Quantum chemical calculations were carried out to elucidate the reaction mechanisms for some typical synthesis.

MeSH terms

Alkylation
Barbiturates / chemical synthesis
Barbiturates / chemistry
Carbon / chemistry*
Heterocyclic Compounds / chemistry*
Models, Chemical
Molecular Structure
Spiro Compounds / chemistry*

Substances

Barbiturates
Heterocyclic Compounds
Spiro Compounds
Carbon
barbituric acid