| 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.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1490–1501, October, 2005. |
