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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)1219-1222
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume55
Issue number5
DOIs
StatePublished - May 1 2018

Fingerprint

Lactams
Byproducts
Condensation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Isolation of 5-Hydroxy-γ-lactams from a Classical 2-Aminopyrrole Synthesis. / Suthiwangcharoen, Nisaraporn; Bean, Andrew C.; Hassan, Minna; Eidell, Cheryl K; Stephens, Chad E.

In: Journal of Heterocyclic Chemistry, Vol. 55, No. 5, 01.05.2018, p. 1219-1222.

Research output: Contribution to journalArticle

Suthiwangcharoen, Nisaraporn ; Bean, Andrew C. ; Hassan, Minna ; Eidell, Cheryl K ; Stephens, Chad E. / Isolation of 5-Hydroxy-γ-lactams from a Classical 2-Aminopyrrole Synthesis. In: Journal of Heterocyclic Chemistry. 2018 ; Vol. 55, No. 5. pp. 1219-1222.
@article{56f7b3bd41cd46c18775217e58412462,
title = "Isolation of 5-Hydroxy-γ-lactams from a Classical 2-Aminopyrrole Synthesis",
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.",
author = "Nisaraporn Suthiwangcharoen and Bean, {Andrew C.} and Minna Hassan and Eidell, {Cheryl K} and Stephens, {Chad E.}",
year = "2018",
month = "5",
day = "1",
doi = "10.1002/jhet.3156",
language = "English (US)",
volume = "55",
pages = "1219--1222",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "5",

}

TY - JOUR

T1 - Isolation of 5-Hydroxy-γ-lactams from a Classical 2-Aminopyrrole Synthesis

AU - Suthiwangcharoen, Nisaraporn

AU - Bean, Andrew C.

AU - Hassan, Minna

AU - Eidell, Cheryl K

AU - Stephens, Chad E.

PY - 2018/5/1

Y1 - 2018/5/1

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85044304721&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85044304721&partnerID=8YFLogxK

U2 - 10.1002/jhet.3156

DO - 10.1002/jhet.3156

M3 - Article

AN - SCOPUS:85044304721

VL - 55

SP - 1219

EP - 1222

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 5

ER -