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Investigation of the Interaction of 5-Aryl-2,3-dihydro-2,3-furandiones with Compounds Containing C=N and C≡N Bonds Simultaneously

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Aroylketenes, generated by the thermolysis of 5-aryl-2,3-dihydro-2,3-furandiones, react with S-methyl-N-cyano-N′-phenylisothiourea, N-cyano-N′,N′-dimethylformamidine, and N,N-bis(β-cyanoethyl)-cyanamide with the formation of 6-aryl-2-[(methylthio)(phenylamino)methylene]amino-, 6-aryl-2-dimethylaminomethyleneamino-, and 6-aryl-2-[N,N-bis(β-cyanoethyl)amino]-4H-1,3-oxazin-4-ones respectively. Modeling has been carried out of the interaction of benzoylketene with the indicated cyano compounds by the SSP MO LCAO semiempirical method using the MNDO-PM3 approach. A mechanism is proposed for the formation of substituted 4H-1,3-oxazin-4-ones.

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Authors and Affiliations

  1. Perm State University, Perm, 614990, Russia

    D. D. Nekrasov & S. N. Shurov

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  1. D. D. Nekrasov
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  2. S. N. Shurov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1490–1501, October, 2005.

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Nekrasov, D.D., Shurov, S.N. Investigation of the Interaction of 5-Aryl-2,3-dihydro-2,3-furandiones with Compounds Containing C=N and C≡N Bonds Simultaneously. Chem Heterocycl Compd 41, 1245–1254 (2005). https://doi.org/10.1007/s10593-005-0310-5

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  • DOI: https://doi.org/10.1007/s10593-005-0310-5

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