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 in | Tetrahedron Vol. 72; no. 20; pp. 2552 - 2559 |
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Format | Journal Article |
Language | English |
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19.05.2016
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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.
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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 KETONES DOUBLE REDUCTION DIELS-ALDER REACTION CONSTRUCTION CYCLIC AROMATIC SULFONAMIDES DERIVATIVES |
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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 |
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