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

All articles of this category 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.