In(OTf)3-Catalyzed One-Pot Tandem Mannich and Conia-Ene Cyclization Reaction of N-Propargyl Amido Alcohols with 1,3-Dicarbonyl Compounds: An Approach To Construct Tetrahydro-1H-pyrrolo[2,1-a]isoindolone-1,1-dicarboxylate and Its Application
| Autor: | Archana Kumari Sahu, Ramanjaneyulu Unnava, Sudip Shit, Anil K. Saikia |
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| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Double bond 010405 organic chemistry Chemistry Organic Chemistry Aromatization Regioselectivity 010402 general chemistry 01 natural sciences Medicinal chemistry Pyrrolidine 0104 chemical sciences chemistry.chemical_compound Cascade reaction Trifluoromethanesulfonate Mannich reaction Ene reaction |
| Zdroj: | The Journal of Organic Chemistry. 85:1961-1971 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.9b02686 |
| Popis: | A one-pot tandem reaction has been developed for the synthesis of substituted tetrahydropyrroloisoindolone via Mannich reaction of N-propargyl amido alcohols with 1,3-dicarbonyl compounds followed by Conia-ene cyclization reaction in moderate to good yields catalyzed by indium(III)triflate [In(OTf)3]. The reaction is highly regioselective with an exo-cyclic double bond in the pyrrolidine ring. The substituted tetrahydropyrroloisoindolone can be converted to 5H-pyrrolo[2,1-a]isoindol-5-one via decarboxylative aromatization reaction. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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