Reductive Cyclization of 2-Cyanomethyl-3-nitrobenzoates

Y.  Woon; C Esther; Archana Dhami; Peter Sunderland; David A Chalkley; Michael Threadgill

doi:10.2174/157017806778559581

Reductive Cyclization of 2-Cyanomethyl-3-nitrobenzoates

Y. Woon, C Esther, Archana Dhami, Peter Sunderland, David A Chalkley, Michael Threadgill

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	3
Pages (from-to)	619-621
Journal	Letters in Organic Chemistry
Volume	3
Issue number	8
DOIs	https://doi.org/10.2174/157017806778559581
Publication status	Published - 1 Aug 2006

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title = "Reductive Cyclization of 2-Cyanomethyl-3-nitrobenzoates",

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.",

author = "Y. Woon and C Esther and Archana Dhami and Peter Sunderland and Chalkley, {David A} and Michael Threadgill",

year = "2006",

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AU - Woon, Y.

AU - Esther, C

AU - Dhami, Archana

AU - Sunderland, Peter

AU - Chalkley, David A

AU - Threadgill, Michael

PY - 2006/8/1

Y1 - 2006/8/1

N2 - 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.

AB - 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.

U2 - 10.2174/157017806778559581

DO - 10.2174/157017806778559581

M3 - Article

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VL - 3

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EP - 621

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 8

M1 - 3

ER -

Reductive Cyclization of 2-Cyanomethyl-3-nitrobenzoates

Abstract

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