Affiliation:
1. Heteroatom Chemistry Department Institute of Organic Chemistry National Academy of Sciences of Ukraine Akademika Kukharya Street 5 Kyiv 02094 Ukraine
2. Department of X-ray Diffraction Study and Quantum Chemistry SSI “Institute for Single Crystals” National Academy of Sciences of Ukraine Nauky ave. 60 Kharkiv 61072 Ukraine
3. Department of Mechanisms of Bioorganic Reactions V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry National Academy of Sciences of Ukraine Akademika Kukharya Street 1 Kyiv 02094 Ukraine
4. I. F. Lab. Ltd. 5 Akademika Kukhara St. 02094 Kyiv Ukraine
Abstract
AbstractA novel simple and effective method has been developed for constructing pyrazolothiadiazine and pyrazolothiadiazepine fused heterocycles incorporating an endocyclic sulfonamide fragment. The cyclocondensation of readily available N‐(chlorosulfonyl)imidoyl chlorides, RC(Cl)=NSO2Cl (R=CCl3, CF2Br), with N‐methyl‐substituted 4‐ or 5‐aminopyrazoles results in the formation of isomeric pyrazolothiadiazine‐S,S‐dioxides. Additionally, when 5‐ or 3‐aminoalkyl‐substituted pyrazoles are employed, they serve as 1,4‐N−C−C−C binucleophiles, leading to the synthesis of novel pyrazolothiadiazepine heterocycles. Notably, the trichloromethyl and bromodifluoromethyl substituents in these compounds can be converted into dichloromethyl and difluoromethyl groups, providing enhanced functionalization options.