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.
Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes / M. Dell'Acqua, V. Pirovano, G. Confalonieri, A. Arcadi, E. Rossi, G. Abbiati. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 12:40(2014 Oct 28), pp. 8019-8030. [10.1039/C4OB01583E]
Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes
M. Dell'Acqua;V. Pirovano;E. Rossi;G. Abbiati
2014
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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