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

Sandra Ferrer, Declan P. Naughton, Ifat Parveen, Michael D. Threadgill

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32 Citations (SciVal)
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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.
Original languageEnglish
Pages (from-to)335-340
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume2
Issue number3
DOIs
Publication statusPublished - 24 Jan 2002
Externally publishedYes

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