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Synthesis 2019; 51(06): 1473-1481
DOI: 10.1055/s-0037-1610999
DOI: 10.1055/s-0037-1610999
paper
Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1H)-one Core
The authors thank CSIR, New Delhi for financial support as part of the XII five-year plan program under the title ACT ().Weitere Informationen
Publikationsverlauf
Received: 01. August 2018
Accepted after revision: 05. September 2018
Publikationsdatum:
14. November 2018 (online)
Abstract
A novel, one-pot reaction for the synthesis of 3,4-dihydroisoquinolin-2(1H)-one derivatives is developed via a base-mediated three-component reaction of ninhydrin, aniline and acetylenic esters. This diastereoselective reaction takes place in methanol at 70 °C under transition-metal-free conditions, and direct construction of the C–N and C–C bonds is readily achieved via tandem cyclization. These cyclic frameworks are resourceful small molecular keys to many natural products.
Key words
ninhydrin - anilines - 3,4-dihydroisoquinolin-2(1H)-ones - methanolysis - tandem cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610999.
- Supporting Information
- CIF File
-
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