1,3-dipolar cycloaddition of nitrones to free and coordinated nitriles: Routes to control the synthesis of 2,3-dihydro-1,2,4-oxadiazoles

Data on 1,3-dipolar cycloaddition of nitrones to free and coordinated nitriles producing 2,3-dihydro-1,2,4-oxadiazoles (or Δ⁴-1,2,4-oxadiazolines) are summarized. The latter compounds belong to the virtually unknown class of heterocyclic systems. The main factors responsible for the cycloaddition reactions are discussed. Particular attention is given to the role of metal centers in controlling the synthesis of 2,3-dihydro-1,2,4-oxadiazoles. Dedicated to Academician O. M. Nefedov on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1803–1815, November, 2006.