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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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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Abstract 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]
AbstractList 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.
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]
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. (C) 2016 Elsevier Ltd. All rights reserved.
Author Keeley, Aaron
Evans, Paul
McCauley, Shane
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Keywords Heck reaction
Sulfonamide
Sultam
Heterocycle
Dehydrogenation
Biaryl
CROSS-METATHESIS
NITROGEN-HETEROCYCLES
FURANS
EXPEDIENT ROUTE
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CONSTRUCTION
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SSID ssj0001123
Score 2.321482
Snippet The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were...
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SubjectTerms Adducts
Biaryl
Chemistry
Chemistry, Organic
Dehydrogenation
Dioxides
Forming
Heck reaction
Heterocycle
Metathesis
Oxidation
Physical Sciences
Pyrroles
Science & Technology
Sulfonamide
Sultam
Synthesis
Tetrahedrons
Title A ring closing metathesis-manganese dioxide oxidation sequence for the synthesis of substituted pyrroles
URI https://dx.doi.org/10.1016/j.tet.2016.03.088
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