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Synthesis 1993; 1993(10): 951-952
DOI: 10.1055/s-1993-25974
short paper
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Ring Transformation of Pyrimidine-4(1H)-thiones with Cyclohexanespiro-3′-oxaziridine: Synthesis of 5-(2-Amino-1-arylethenyl)-1,2,4-thiadiazoles

Michael Pätzel* , Jürgen Liebscher
  • *Fachbereich Chemie, Humboldt-Universität zu Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany
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Publication Date:
29 April 2002 (online)

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Pyrimidine-4 (1H)-thiones 2 react with cyclohexanespiro-3′-oxaziridine (3) by S-amination and ring transformation to give 5-(2-amino-1-arylethenyl)-1,2,4-thiadiazoles 5. Reactions of the precursors of 2, i. e. N-(3-aminothioacryloyl)formamidines 1, with cyclohexanespiro-3′-oxaziridine (3) mostly gave complex reaction mixtures containing the expected thiadiazoles 6, isomeric 5-formamidino-1,2-thiazoles 8, the 5-formylamino-1,2-thiazole 9 or 3-pyrrolidinocinnamonitrile 10.