Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes?

Organic & Biomolecular Chemistry Pub Date: 2014-09-03 DOI: 10.1039/C4OB01583E

Abstract

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.

Graphical abstract: Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes
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