Synthesis method of pyrrolo tetrahydroquinoline compound containing perfluoroalkane structure
By reacting di-tert-butyldiazaproleone and perfluoroiodoalkane with 1.7-enyne under the conditions of palladium catalyst, cesium carbonate and phosphine ligand, the problem of difficult synthesis of pyrrolotetrahydroquinoline compounds containing perfluoroalkane structure in the prior art was successfully solved, and an efficient and simple synthesis process was achieved.
CN119751455AActive Publication Date: 2025-04-04CHANGZHOU UNIV
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Patent Information
- Application Number
- CN202411949719.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-27
- Publication Date
- 2025-04-04
- Estimated Expiration
- 2044-12-27
AI Technical Summary
Technical Problem
It is difficult to effectively synthesize pyrrolotetrahydroquinoline compounds containing perfluoroalkane structures in the prior art.
Method used
Di-tert-butyldiazaprolinone is used as the nitrogen source and perfluoroiodoalkanes as the fluorine source. Under the conditions of a palladium catalyst, cesium carbonate and phosphine ligand, pyrrolotetrahydroquinoline compound containing perfluoroalkanes and di-tert-butyldiazaprolinone is obtained by reacting a 1.7-enyne compound with perfluoroiodoalkanes and di-tert-butyldiazaprolinone.
Benefits of technology
The efficient synthesis of the corresponding pyrrolotetrahydroquinoline compounds and their derivatives is achieved, with simple steps, easy operation and high synthesis efficiency.
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Abstract
The invention relates to the technical field of organic medicine synthesis, and discloses a synthetic method of a pyrrolo tetrahydroquinoline compound containing a perfluoroalkane structure. The synthesis method comprises the following steps: under the protection of inert gas, adding 1.7-enyne, di-tert-butyl diaziridone, perfluoroalkyl iodide, a palladium catalyst, a ligand and alkali into an organic solvent according to a ratio, reacting at a heating temperature, and preparing the pyrrolo tetrahydroquinoline compound containing the perfluoroalkane structure as shown in the following formula after the reaction. And separating a target product after the reaction is completed. According to the invention, di-tert-butyldiazidinone is used as a nitrogen source, perfluoroalkyl iodide is used as a fluorine source, the method has the advantages of simplicity and novelty, and a series of pyrrolo tetrahydroquinoline compounds containing perfluoroalkane structures and derivatives thereof can be synthesized with extremely high efficiency.
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