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Isolation of 5‐Hydroxy‐γ‐lactams from a Classical 2‐Aminopyrrole Synthesis
Author(s) -
Suthiwangcharoen Nisaraporn,
Bean Andrew C.,
Hassan Minna,
Eidell Cheryl K.,
Stephens Chad E.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3156
Subject(s) - chemistry , thionyl chloride , yield (engineering) , lactam , beta lactam , aminoketone , methylene , condensation , ethyl cyanoacetate , stereochemistry , chloride , organic chemistry , catalysis , antibiotics , malononitrile , materials science , physics , metallurgy , thermodynamics , biochemistry
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.