Synthesis 1988; 1988(8): 636-640
DOI: 10.1055/s-1988-27663
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
20 August 2002 (online)

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.

    >