Novel Method for the Preparation of 2h-1,2,4-Benzothiadiazin-3(4h)-One 1,1-Dioxides via a Curtius Rearrangement

Chemistry of Heterocyclic Compounds 2012
Jekaterīna Ivanova, Raivis Žalubovskis, Igor Vozny, Peteris Trapencieris, Diana Borovika

1,2,4-Benzothiadiazines are known for their antiviral activity, hence work on their synthesis has been carried out for quite some time. Hence in the study it was shown that a series of 1,2,4-benzo-thiadiazinones could be prepared by the reaction of anilines with chlorosulfonyl isocyanate and cyclization of the N-chlorosulfonyl ureas. More recently the palladium-catalyzed cyclocarbonylation of o-aminobenzenesulfon-amides has been reported. We have developed a novel method for the preparation of the 2H-1,2,4-benzo-thiadiazin-3(4H)-one 1,1-dioxides from saccharin derivatives, the key stage of which is a Curtius rearrangement followed by an intramolecular cyclization.

Atslēgas vārdi
2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide | Acylazide | Curtius rearrangement | Hydrazide | Intramolecular cyclization | Saccharin
DOI
10.1007/s10593-012-1108-x
Hipersaite
http://link.springer.com/article/10.1007%2Fs10593-012-1108-x

Ivanova, J., Žalubovskis, R., Vozny, I., Trapencieris, P., Borovika, D. Novel Method for the Preparation of 2h-1,2,4-Benzothiadiazin-3(4h)-One 1,1-Dioxides via a Curtius Rearrangement. Chemistry of Heterocyclic Compounds, 2012, Vol.48, Iss.7, 1114.-1116.lpp. ISSN 0009-3122. Pieejams: doi:10.1007/s10593-012-1108-x

Publikācijas valoda
English (en)