Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles
| Autor: | Craig D. Smith, Michael H. R. Beh, Alison Thompson, Min Joon Kim, Sophie M. Gaube |
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| Rok vydání: | 2019 |
| Předmět: |
Decarboxylation
General Chemical Engineering chemistry.chemical_element 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences Formylation chemistry.chemical_compound Nickel Hydrolysis chemistry Functional group Organic chemistry Reactivity (chemistry) 0210 nano-technology |
| Zdroj: | RSC Advances. 9:31773-31780 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c9ra07527e |
| Popis: | 2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesised using a Knorr-type approach from aliphatic starting materials. 2-Thionoester pyrroles were reduced to the corresponding 2-formyl pyrroles, or the deuterated formyl variant, in one step using RANEY® nickel, thereby removing the need for the much-utilised hydrolysis/decarboxylation/formylation steps that are typically required to convert Knorr-type 2-carboxylate pyrroles into 2-formyl pyrroles. 2-Thionoester pyrroles proved tolerant of typical functional group interconversions for which the parent 2-carboxylate pyrroles have become known. |
| Databáze: | OpenAIRE |
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