Abstract
In the reaction of N-methylquinoxalinium iodide with acetylacetone at −30 °C, the formation of 3-acetyl-2,4-dimethyl-3a,4,9,9a-tetrahydrofuro[2,3-b]quinoxaline has been recorded by 1H NMR spectroscopy, this being a regioisomer of the 3-acetyl-2,9-dimethyl-3a,4,9,9a-tetrahydro[2,3-b]quinoxaline formed in this reaction at temperatures above −10 °C. σ-Adducts of the N-methylquinoxalinium cation with alcohols, amines, and β-diketones have also been identified, and their role in cyclizations leading to the annelation of a furan ring is discussed.
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For Communication 15, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 669–677, May, 1985.
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Charushin, V.N., Ponizovskii, M.G., Chupakhin, O.N. et al. Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 16. σ-adducts of quinoxalinium salts with amines, alcohols, and enolates and their role in cyclizations with β-dicarbonyl compounds. Chem Heterocycl Compd 21, 564–572 (1985). https://doi.org/10.1007/BF00506075
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DOI: https://doi.org/10.1007/BF00506075