Synthesis 1993; 1993(11): 1129-1132
DOI: 10.1055/s-1993-26014
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Dihalogentriphenylphosphorane in der Heterocyclensynthese; 271: Heterokondensierte 1,2,4-Triazolo[1,5-c]pyrimidine aus Enaminonitrilen via O-Ethylformimide

Heinrich Wamhoff* , Elmar Kroth, Christof Strauch
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn 1, Germany
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Publikationsdatum:
29. April 2002 (online)

Heterocondensed 1,2,4-Triazolo[1,5-c]pyrimidines from Enamino Nitriles, via O-Ethylformimides By treatment with triethyl orthoformate the enamino nitriles 1, 6 and 12 are converted into the O-ethylformimides 2, 7 and 13. Reaction with semicarbazide gives the heterocondensed pyrimidines 3, 9 and 14, which are in turn cyclized with dichlorotriphenylphosphorane to afford the 1,2,4-triazolo[1,5-c]pyrimidines 4, 10 and 15; hydrolysis of the iminophosphoranes leads to the free amines 5, 11 and 16.