Studies on the Transesterification and Macrolactonization of 2-Pyridyl Esters by Intramolecular N-Alkylation or Metal Ion Coordination

Abstract

In a process analogous to use of the Mukaiyama reagent, ω-hydroxyalkyl 2-pyridyl ester derivatives were converted into lactones by N-alkylation or the coordination of copper(II) triflate and transacylation of the resultant electrophilic ω-hydroxyalkanecarboxypyridinium salts.

lactonization - 2-pyridyl ester - copper(II) triflate - tetrahydr­oquinolizinone

References

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Sample identical (TLC, ¹H and ¹³C NMR, GC-MS) with a commercial sample.

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Sample identical (TLC, ¹H and ¹³C NMR, GCMS) with the lactone intermediate in the synthesis of 24.