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Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes. | LitMetric

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

Org Biomol Chem

Dipartimento di Scienze Farmaceutiche - Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano, via G. Venezian, 21 - 20133 Milano, Italy.

Published: October 2014

AI Article Synopsis

  • An easy method for creating uncommon 2-propargylbenzaldehydes was established, which serve as effective building blocks.
  • These compounds are used to synthesize 3-benzyl isoquinolines through a microwave-assisted process involving domino imination and cycloisomerization with ammonium acetate.
  • A small collection of 3-benzyl isoquinolines was successfully produced in good yields using mild conditions, and two possible reaction mechanisms were suggested.

Article 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.

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Source
http://dx.doi.org/10.1039/c4ob01583eDOI Listing

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