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LOCATION:Online
DESCRIPTION:Acyl(imidoyl)ketenes are highly reactive heterocumulenes that enable diversity-oriented synthesis of various drug-like heterocycles. Such ketenes\, bearing heterocyclic substituents\, afford angularly fused pyridin-2(1H)-ones in their [4+2]-cyclodimerization reactions. We have utilized this property for the development of a new synthetic approach to pharmaceutically interesting pyrido[2\,1-b][1\,3]benzothiazol-1-ones via the [4+2]-cyclodimerization of acyl(1\,3-benzothiazol-2-yl)ketenes generated in situ. The thermal behaviors of 3-aroylpyrrolo[2\,1-c][1\,4]benzothiazine-1\,2\,4-triones and 3-benzoylpyrrolo[2\,1-b][1\,3]benzothiazole-1\,2-dione (two new types of [e]-fused 1H-pyrrole-2\,3-diones) have been studied by thermal analysis and HPLC  to elucidate their capability to be a source of acyl(1\,3-benzothiazol-2-yl)ketenes. As a result\, we have found that only 3-aroylpyrrolo[2\,1-c][1\,4]benzothiazine-1\,2\,4-triones are suitable for this. The experimental results are supplemented with computational DFT studies of the possible  reaction mechanisms that demonstrate that thermolysis of 3-aroylpyrrolo[2\,1-c][1\,4]benzothiazine-1\,2\,4-triones proceeds through an unprecedented cascade of two thermal decarbonylations.
DTSTART:20231202T100000Z
DTEND:20231202T110000Z
SUMMARY:Seminar “Approach to pyrido[2\,1-b][1\,3]benzothiazol-1-ones via in situ generation of acyl(1\,3-benzothiazol-2-yl)ketenes by thermolysis of pyrrolo[2\,1-c][1\,4]benzothiazine-1\,2\,4-triones: experimental and theoretical studies”
URL;VALUE=URI:/media/events/seminar-approach-to-pyrido21-b13benzothiazol-1-ones-via-in-situ-generation-of-acyl13-benzothiazol-2-ylketenes-by-thermolysis-of-pyrrolo21-c14benzothiazine-124-triones-experimental-and-theoretical-studies/
DTSTAMP:20250428T003201Z
UID:680ea251e9c1d
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