Issue 3, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Sandra Ferrer,a   Declan P. Naughton,b   Ifat Parveenc  and  Michael D. Threadgill*c  

* Corresponding authors

a Department of Medical Sciences, University of Bath, Claverton Down, Bath, UK

b School of Pharmacy & Biomolecular Sciences, University of Brighton, Brighton, UK

c Department of Pharmacy & Pharmacology, University of Bath, Claverton Down, Bath, UK
E-mail: m.d.threadgill@bath.ac.uk
Fax: +44 1225 826114

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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Article information

DOI
https://doi.org/10.1039/B109776H
Article type
Paper
Submitted
26 Oct 2001
Accepted
03 Dec 2001
First published
03 Jan 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 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, 335 DOI: 10.1039/B109776H

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