Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane

2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2–4 h), the yields of pyrroles ranging 11–85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the...

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Bibliographic Details
Published in:Tetrahedron 2015-01, Vol.71 (1), p.124-128
Main Authors: Trofimov, Boris A., Mikhaleva, Al'bina I., Ivanov, Andrei V., Shcherbakova, Viktoria S., Ushakov, Igor' A.
Format: Article
Language:English
Subjects:
1,2-Dichloroethane
Aliphatic compounds
Hydrochlorides
Ketones
Pyrroles
Superbases
Synthesis (chemistry)
Tetrahedrons
Trofimov reaction
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Summary:2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2–4 h), the yields of pyrroles ranging 11–85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the reaction conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.11.031