Abstract
The reaction of imido esters that contain an active methylene group with four isomeric benzodiazinium cations, viz., the 1-methylquinoxalinium, 2-methylcinnolinium, 3-methylquinazolinium, and 2-methylphthalazinium cations, was investigated. The 1-methylquinoxalinium cation reacts with imido esters via a scheme involving anionic [3− +2]-cycloaddition to form tetrahydropyrrolo[2,3-b]quinoxalines. The 2-methylcinnolinium cation forms an adduct with an annelated pyrrole ring. Under the influence of imido esters, the 3-methylquinazolinium cation undergoes recyclization to a 2,3-disubstituted quinoline. The 2-methylphthalazinium cation is inert in this reaction.
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See [1] for Communication 4.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1549–1553, November, 1981.
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Chupakhin, O.N., Charushin, V.N., Naumova, L.M. et al. Cyclization of n-alkylazinium cations with bisnucleophiles. 5. Cyclic adducts and recyclization products in the reactions of benzodiazinium cations with imido esters. Chem Heterocycl Compd 17, 1134–1138 (1981). https://doi.org/10.1007/BF00506467
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DOI: https://doi.org/10.1007/BF00506467