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Synthesis 1985; 1985(9): 861-867
DOI: 10.1055/s-1985-31365
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Heterocyclen-Synthesen mit Monothiomalonsäure-Amiden: Synthese von 3-Oxo-2,3-dihydroisothiazolo [5,4-b] pyridinen und 3-Oxo-2,3-dihydroisothiazolo[5,4-d]pyrimidinen

Wolfgang Schaper*
  • *Hauptlaboratorium HOECHST AG, D-6230 Frankfurt/Main 80, Bundesrepublik Deutschland
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Publication Date:
27 September 2002 (online)

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Heterocyclic Syntheses with Monothiomalonic Amides: Synthesis of 3-Oxo-2,3-dihydroisothiazolo[5,4-b]pyridines and 3-Oxo-2,3-dihydroisothiazolo[5,4-d]pyrimidines The monothiomalonic acid amides 5, prepared from cyanoacetamides 4 and hydrogen sulphide, react with diketones 6 or aldehyde derivatives 7 to give the 2-thioxo-1,2-dihydropyridine-3-carboxamides 8 which can be cyclised to the 3-oxo-2,3-dihydroisothiazolo[5,4-d]pyridines 2. Amides 5 also react with s-triazine to give the 3-oxo-2,3-dihydroisothiazolo [5,4-d]pyrimidines 3.