Reductive Cyclisation of 2-Cyanomethyl-3-Nitrobenzoates

Title: Reductive Cyclisation of 2-Cyanomethyl-3-Nitrobenzoates

Volume: 3 Issue: 8

Author(s): Esther C. Y. Woon, Archana Dhami, Peter T. Sunderland, David A. Chalkley and Michael D. Threadgill

Affiliation:

Keywords: Reductive cyclisation, isoquinolinone, isoquinoline, DiBAL-H

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-1 inhibitor 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.

Cite this article as:

Y. Woon C. Esther, Dhami Archana, Sunderland T. Peter, Chalkley A. David and Threadgill D. Michael, Reductive Cyclisation of 2-Cyanomethyl-3-Nitrobenzoates, Letters in Organic Chemistry 2006; 3 (8) . https://dx.doi.org/10.2174/157017806778559581