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Synthesis 2008(11): 1688-1702  
DOI: 10.1055/s-2008-1067048
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Focused Microwave Approach to the Synthesis of Amino-Substituted Pyrroloisoquinolines and Pyrroloquinolines via a Sequential Multi-Component Coupling Process

Mark D. Hopkin, Ian R. Baxendale, Steven V. Ley*
Innovative Technology Centre (ACS), Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
Further Information

Publication History

Received 25 February 2008
Publication Date:
29 April 2008 (online)

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Abstract

A multi-component reaction has been developed allowing direct access to pyrroloisoquinolines and pyrroloquinolines with new, electron-rich substitution patterns. The synthesised amino-substituted heterocyclic compounds and intermediates involved in their formation represent novel compounds. Focused microwave irradiation was used extensively to allow simple access to a wide temperature range using low boiling point solvents.

Key words

focused microwave irradiation - fused-ring systems - heterocycles - multi-component reactions - pyrroloisoquinolines - solid-supported reagents

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27

The reactions showed excellent conversions, but isolation of the final compounds proved problematic.

30

Diethylaminomethyl polystyrene (3.2 mmol g-1) is commercially available from Fluka (website:
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31

Crystallised from CH2Cl2-hexane.

33

PS-SO3H is a macroporous polymer-supported sulfonic acid (4.45 mmol g-1) available from Biotage (website:
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36

Biotage (website: http://www.biotage.com).

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Varian, Inc. (website: http://www.varianinc.com).

38

Crystallographic data for 6d have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 678909 (Authors: J. E. Davies, M. D. Hopkin, S. V. Ley). Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or
e-mail: deposit@ccdc.cam.ac.uk).

39

Crystallographic data for 10da have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 678908 (Authors: J. E. Davies, M. D. Hopkin, S. V. Ley). Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or
e-mail: deposit@ccdc.cam.ac.uk).