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Synthesis 1988; 1988(8): 636-640
DOI: 10.1055/s-1988-27663
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1,2,3,6 Tetrahydropyridine durch [4 + 2]-Cycloaddition von 1-Alkoxy-1,3-dienen und (Tosyloxyimino)malodinitril

Walter Dormagen* , Klaus Rotscheidt, Eberhard Breitmaier
  • *Institut für Organische Chemie und Biochemie der Universität Bonn Gerhard-Domagk-Straße 1, D-5300 Bonn, Federal Republic of Germany
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Publication Date:
20 August 2002 (online)

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1,2,3,6-Tetrahydropyridines by [4 + 2] Cycloaddition of 1-Alkoxy-1,3-dienes and (Tosyloxyimino)malononitrile 1-Alkoxy-1,3-alkadienes and 5-vinyl-3,4-dihydro-2H-pyran (prepared by Wittig carbonyl olefination of 3-alkoxyacroleins and 5-formyl-3, 4-dihydro-2H-pyran) undergo [4 + 2] cycloaddition with (tosyloxyimino) -malononitrile in tetrahydrofuran/water at room temperature to give 5-alkyl-2, 2-dicyano-6-ethoxy-1-tosyloxy-1,2,3,6-tetrahydropyridines and 7,7-dicyano-8-tosyloxy-3, 4,6,7,8,8a-hexahydro-2H-pyrano[2,3-b]pyridine. These compounds can be converted into 6-alkoxy-5-alkyl-2,2-dicyano-2,3-dihydropyridines and pyridine-2-carboxamides, respectively.