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Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines.

ABSTRACT: An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-meta-substituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.

SUBMITTER: Arcadi A 

PROVIDER: S-EPMC8199670 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of <i>N</i>-Ethoxycarbonyl-<i>N</i>-Propargylanilines.

Arcadi Antonio A   Calcaterra Andrea A   Fabrizi Giancarlo G   Fochetti Andrea A   Goggiamani Antonella A   Iazzetti Antonia A   Marrone Federico F   Marsicano Vincenzo V   Mazzoccanti Giulia G   Serraiocco Andrea A  

Molecules (Basel, Switzerland) 20210602 11

An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of <i>N</i>-ethoxycarbonyl protected-<i>N</i>-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-<i>endo</i> cyclization product in good to high yields. In the presence of <i>N</i>-ethoxycarbonyl-<i>N</i>-propargyl-<i>meta-</i>substituted anilines, the regiodivergent cyclization at the <i>ortho</i>-/<i>para</i>-positi  ...[more]

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