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Synthesis 1993; 1993(5): 525-529
DOI: 10.1055/s-1993-25898
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Ring Chain Transformations; XI:1 Synthesis of Semicyclic 3-(Aminoalkylideneamino)-3-aryl-2-propenenitriles and Their Ring Chain Transformation to 2-(ω-Aminoalkyl)-6-aryl-4-halo-5-pyrimidinecarbonitriles

Michael Pätzel* , Alexej Ushmajev, Jürgen Liebscher
  • *Institut für Organische Chemie, Fachbereich Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D-1040 Berlin, Germany
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Publication Date:
17 September 2002 (online)

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Semicyclic 3-aryl-2-aza-3-methylthio-2-propeniminium iodides 1 react with CH-acidic acetonitriles 2 by elimination of methanethiol affording 3-(1-alkyl-2-pyrrolidinylideneamino)-, 3-(1-alkyl-2-piperidinylideneamino)- and 3-(1-alkylhexahydro-1H-azepin-2-ylidene-amino)-3-aryl-2-propenenitriles 3. Further addition of hydrogen halides to the cyano group of 2-cyano-substituted 3 gives rise to a ring chain transformation reaction. The resulting 4-halo-2-[ω-(methylamino) alkyl]-5-pyrimidinecarbonitrile hydrohalides 7 can be isolated or hydrolyzed during workup to 3,4-dihydro-2-[ω-(methylamino)alkyl]-4-oxo-5-pyrimidinecarbonitrile hydrohalides 8. Interaction of amines with the 4-halopyrimidines 7 causes either reversed ring chain transformation to the starting compounds 3 or substitution of the halo-substituent resulting in the corresponding 4-amino-2-[ω-(methylamino) alkyl]-5-pyrimidine carbonitrile hydrohalides 10.