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Synlett 1990; 1990(7): 401-403
DOI: 10.1055/s-1990-21106
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Synthesis of Pyrimidines Bearing Sterically Demanding Substituents from Azetes and Nitriles1

Udo Hees* , Martin Ledermann, Manfred Regitz
  • *Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-6750 Kaiserslautern, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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Two kinetically stabilized azetes 1a,b react with acceptor-substituted nitrites 2a-g to furnish tetra-substituted pyrimidines 4a-i; the primarily formed Dewar pyrimidines 3 were not detected. In the reactions with α-methylenenitriles, competing 1,4-addition reactions take place and push-pull 1,3-butadiene 6 and 2-aza-1,3-butadiene 8 were prepared from the non-isolable 2-azetines 5.