Journal of Heterocyclic Chemistry 2018-03-22

Isolation of 5‐Hydroxy‐γ‐lactams from a Classical 2‐Aminopyrrole Synthesis

Nisaraporn Suthiwangcharoen; Andrew C. Bean; Minna Hassan; Cheryl K. Eidell; Chad E. Stephens

Index: 10.1002/jhet.3156

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Abstract

5‐hydroxy‐γ‐lactams have been isolated as major byproducts from a classical 2‐aminopyrrole synthesis involving condensation of an in situ prepared α‐aminoketone with methyl cyanoacetate. The classical 2‐aminopyrrole was obtained in very low yield, or not at all. One 5‐hydroxy‐γ‐lactam was dehydrated to the known 5‐methylene‐γ‐lactam in good yield using thionyl chloride.