112382-20-4Relevant academic research and scientific papers
Reaction of Sulfenes with Heterocyclic N,N-Disubstituted α-Aminomethyleneketones. XIII. Synthesis of 1,2-Oxathiinoquinazoline Derivatives
Menozzi, Giulia,Bargagna, Alberto,Mosti, Luisa,Schenone, Pietro
, p. 633 - 635 (2007/10/02)
The 1,4-cycloaddition of sulfene to N,N-disubstituted (E)-6-aminomethylene-7,8-dihydro-(2-methyl)-(2-phenyl)quinazolin-5(6H)-ones I gave N,N-disubstituted 4-amino-3,4,5,6-tetrahydro-(8-methyl)(8-phenyl)-1,2-oxathiinoquinazoline 2,2-dioxides II, which are derivatives of the new heterocyclic system 1,2-oxathiinoquinazoline.With 2-phenylenaminones Id-h, the cycloaddition occured, generally in satisfactory yields, both in the case of aliphatic N,N-disubstitution and aromatic N-monosubstitution, whereas with methyl enaminones Ia-c the reaction took place in low yields only in the case of aliphatic N,N-disubstitution.Also the reaction of 2-phenyl enaminones Id-g with chlorosulfene occurred as with sulfene, giving a mixture of cycloadducts which were dehydrochlorinated in situ with DBN to afford N,N-disubstituted 4-amino-5,6-dihydro-8-phenyl-1,2-oxathiinoquinazoline 2,2-dioxides III generally in satisfactory yields.Compounds III could not be dehydrogenated either by DDQ in boiling benzene or by palladium on carbon in boiling p-cymene.
