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Issue 3, 2002
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N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

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Abstract

Regioselective methods were investigated to prepare N- and O-alkylated isoquinolin-1-ones efficiently. The predicted regioselective alkylation of the nitrogen with (hetero)benzyl halides was complemented using (hetero)benzylic Mitsunobu electrophiles to alkylate predominantly at the oxygen. A series of drug-delivery conjugates was prepared demonstrating control over the site of alkylation. The Mitsunobu reaction provides a new approach to 1-alkoxyisoquinolines that were unavailable via previous harsher synthetic methods.

Graphical abstract: N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

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Publication details

The article was received on 26 Oct 2001, accepted on 03 Dec 2001 and first published on 03 Jan 2002


Article type: Paper
DOI: 10.1039/B109776H
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 335-340

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    N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

    S. Ferrer, D. P. Naughton, I. Parveen and M. D. Threadgill, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 335
    DOI: 10.1039/B109776H

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