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-1 H -pyrrolo[2,1- a ]isoindolone-1,1-dicarboxylate and Its Application

A one-pot tandem reaction has been developed for the synthesis of substituted tetrahydropyrroloisoindolone via Mannich reaction of -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) ]...

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Published inJournal of organic chemistry Vol. 85; no. 4; pp. 1961 - 1971
Main Authors Sahu, Archana Kumari, Unnava, Ramanjaneyulu, Shit, Sudip, Saikia, Anil K
Format Journal Article
LanguageEnglish
Published United States 21.02.2020
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Summary:A one-pot tandem reaction has been developed for the synthesis of substituted tetrahydropyrroloisoindolone via Mannich reaction of -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) ]. The reaction is highly regioselective with an exo-cyclic double bond in the pyrrolidine ring. The substituted tetrahydropyrroloisoindolone can be converted to 5 -pyrrolo[2,1- ]isoindol-5-one via decarboxylative aromatization reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02686