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Synthesis 1993; 1993(1): 75-76
DOI: 10.1055/s-1993-25799
short paper
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Synthesis of Pyrimido[2,1-b]benzoxazolium, Pyrimido[2,1-b]benzothiazolium and Pyrimido[1,2-a]benzimidazolium Salts by Reaction of 3-Isothiocyanato-2-propeniminium Salts with o-Functionalized Anilines

Beate Riemer* , Jürgen Liebscher
  • *Fachbereich Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D(O)-1040 Berlin, Germany
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Publication Date:
17 September 2002 (online)

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3-Isothiocyanato-2-propeniminium salts 1 react with o-phenylenediamine, o-aminophenol or o-aminothiophenol to give o-substituted 1-phenyl-2(1H)-pyrimidinethiones 4, which cyclize upon treatment with methyl iodide to afford pyrimido[2,1-b]benzoxazolium, pyrimido[2,1-b]benzothiazolium and pyrimido[1,2-a]benzimidazolium salts 5 (X = O, S or NH, respectively) by a new condensation reaction.