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RESEARCH PRODUCT

ChemInform Abstract: C-C versus C-N Annulation Reactions of 2-Alkyl-2-oxazolines and 2-Alkyl-2-thiazolines: A Simple Synthesis of Novel 3-Aminoindene, Phthalimidine, Pyrrolidine, and Piperidine Derivatives.

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The effect of various aromatic and aliphatic dielectrophiles on the lithium azaenolates of 2-alkyl-2-oxazolines and 2-alkyl-2-thiazolines has been examined. This effect varies greatly, depending on the nature of the dielectrophile used. 3-Aminoindene (3) and 3-alkylidenephthalimidine (4−5) derivatives were formed as a result of the reactions with dielectrophiles derived from ortho-substituted benzonitriles. Similarly, 2-alkylidenepyrrolidine (7) and 2-alkylidenepiperidine (8) derivatives were obtained in high yields from 2-alkyl-2-oxazolines or 2-alkyl-2-thiazolines and aliphatic dielectrophiles derived from ω-haloalkyldiphenylacetonitrile. C−C versus C−N annulation reactions are discussed.