Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydesElectronic supplementary information (ESI) available. See DOI: 10.1039/c4ob01583e

An easy entry to uncommon 2-propargylbenzaldehydes was developed. 2-Propargylbenzaldehydes demonstrated to be suitable building blocks for the synthesis of 3-benzyl isoquinolines by microwave promoted domino imination/cycloisomerisation in the presence of ammonium acetate. A small library of 3-benzy...

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Main Authors: Dell'Acqua, Monica, Pirovano, Valentina, Confalonieri, Giorgio, Arcadi, Antonio, Rossi, Elisabetta, Abbiati, Giorgio
Format: Article
Language:English
Online Access:Get full text
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Summary:An easy entry to uncommon 2-propargylbenzaldehydes was developed. 2-Propargylbenzaldehydes demonstrated to be suitable building blocks for the synthesis of 3-benzyl isoquinolines by microwave promoted domino imination/cycloisomerisation in the presence of ammonium acetate. A small library of 3-benzyl isoquinolines was obtained in good yields under mild reaction conditions. Two alternative plausible reaction mechanisms are proposed. A modular entry to 2-propargylbenzaldehydes and their use in μW-promoted cascade reaction with ammonium acetate for the synthesis of 3-benzylisoquinolines.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01583e