A ring closing metathesis-manganese dioxide oxidation sequence for the synthesis of substituted pyrroles

The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were obtained for a variety of substituents and the procedure may also be conducted in one-pot. 2-Bromo N-sulfonyl adducts prepared in this manner were...

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Bibliographic Details
Published inTetrahedron Vol. 72; no. 20; pp. 2552 - 2559
Main Authors Keeley, Aaron, McCauley, Shane, Evans, Paul
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.05.2016
Elsevier
Subjects
Adducts
Biaryl
Chemistry
Chemistry, Organic
Dehydrogenation
Dioxides
Forming
Heck reaction
Heterocycle
Metathesis
Oxidation
Physical Sciences
Pyrroles
Science & Technology
Sulfonamide
Sultam
Synthesis
Tetrahedrons
Heck reaction
Sulfonamide
Sultam
Heterocycle
Dehydrogenation
Biaryl
CROSS-METATHESIS
NITROGEN-HETEROCYCLES
FURANS
EXPEDIENT ROUTE
KETONES
DOUBLE REDUCTION
DIELS-ALDER REACTION
CONSTRUCTION
CYCLIC AROMATIC SULFONAMIDES
DERIVATIVES
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Summary:The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were obtained for a variety of substituents and the procedure may also be conducted in one-pot. 2-Bromo N-sulfonyl adducts prepared in this manner were subjected to an intramolecular Heck-type cyclisation, forming cyclic sulfonamides. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.03.088