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Synthesis 1987; 1987(1): 68-70
DOI: 10.1055/s-1987-27850
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Cyclization under Michael Reaction Conditions; II Synthesis of 2-Azabicyclo[2.2.2]octa-2,5-diene Derivatives from Alkylidenemalononitriles and Formation of Pyridine Derivatives

Minoru Igarashi* , Yoshiharu Nakano, Kazuhiro Takezawa, Takeshi Watanabe, Shoichi Sato
  • *Department of Chemistry, Ibaraki University, Mito, Ibaraki, Japan
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Publication Date:
20 August 2002 (online)

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2-Azabicyclo[2.2.2]octa-2,5-diene derivatives 2 are obtained from alkylidenemalononitriles using sodium methoxide. Several of these bicyclo compounds smoothly undergo retro-Diels-Alder with the loss of the hydrocarbon moiety to give the corresponding pyridine derivatives 3 when heated in xylene or acetic acid.

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