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

doi:10.1002/jhet.3156

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	1219-1222
Number of pages	4
Journal	Journal of Heterocyclic Chemistry
Volume	55
Issue number	5
DOIs	https://doi.org/10.1002/jhet.3156
State	Published - May 2018

ASJC Scopus subject areas

Organic Chemistry

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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.",

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AU - Bean, Andrew C.

AU - Hassan, Minna

AU - Eidell, Cheryl K.

AU - Stephens, Chad E.

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AB - 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.

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

Abstract

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