An Efficient Method for the Programmed Synthesis of Multifunctional Diketopyrrolopyrroles
| Autor: | Michał Pieczykolan, Bartłomiej Sadowski, Daniel T. Gryko |
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| Rok vydání: | 2020 |
| Předmět: |
Steric effects
chemistry.chemical_classification Primary (chemistry) Nitrile 010405 organic chemistry Chemistry General Medicine General Chemistry 010402 general chemistry 01 natural sciences Aldehyde Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Diethyl Oxalacetate Reactivity (chemistry) |
| Zdroj: | Angewandte Chemie International Edition. 59:7528-7535 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201915953 |
| Popis: | A new, transformative methodology for the preparation of diketopyrrolopyrroles from aldehydes, primary amines, nitriles, and diethyl oxalacetate has been developed. It is now possible to prepare diketopyrrolopyrroles bearing an ordered arrangement of three different substituents from abundant and commercially available materials, allowing the independent regulation of all desired physicochemical properties. For the first time very electron-rich (carbazol-3-yl, dimethylaminophenyl, pyrrolo[3,2-b]pyrrolyl), and sterically hindered substituents (naphthalen-1-yl, quinolin-4-yl, acridin-9-yl, imidazo[1,5-a]pyridin-1-yl, 2-bromophenyl etc.) can be appended to the diketopyrrolopyrrole core by condensation of an appropriate nitrile with a pyrrolidin-2-one intermediate. Even greater synthetic possibilities are related to the fact that such demanding substituents as 4-dimethylaminophenyl, indol-3-yl, and 2-methoxyphenyl can be incorporated from aldehyde precursors, bypassing problems with the nitriles reactivity. |
| Databáze: | OpenAIRE |
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