Title of article
Reductive Cyclisation of 2-Cyanomethyl-3-Nitrobenzoates
Author/Authors
Woon, Esther C.Y. University of Bath - Department of Pharmacy Pharmacology, UK , Dhami, Archana University of Bath - Department of Pharmacy Pharmacology, UK , Sunderland, Peter T. University of Bath - Department of Pharmacy Pharmacology, UK , Chalkley, David A. University of Bath - Department of Pharmacy Pharmacology, UK , Threadgill, Michael D. University of Bath - Department of Pharmacy Pharmacology, UK
From page
619
To page
621
Abstract
Selective reduction of the nitrile in methyl 2-cyanomethyl-3-nitrobenzoate with DiBAL-H at low temperature, followed by cyclisation in situ gave 5-nitroisoquinolin-1-one, leading towards the lead PARP-1inhibitor 5-AIQ. However, increasing steric bulk at the methylene switched reduction to the ester only, giving the corresponding benzaldehyde. Surprisingly, increasing steric bulk in the ester also allowed reduction of the ester prior to cyclisation, giving 5-nitroisoquinoline.
Keywords
Reductive cyclisation , isoquinolinone , isoquinoline , DiBAL , H
Journal title
letters in organic chemistry
Journal title
letters in organic chemistry
Record number
2718050
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