Reductive cyclisation of 2-cyanomethyl-3-nitrobenzoates

E C Y Woon; A Dhami; P T Sunderland; D A Chalkley; M D Threadgill

doi:10.2174/157017806778559581

Reductive cyclisation of 2-cyanomethyl-3-nitrobenzoates

E C Y Woon
, A Dhami
, P T Sunderland
, D A Chalkley
, M D Threadgill

Department of Life Sciences

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

5 Citations (SciVal)

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

Access to Document

10.2174/157017806778559581

Cite this

@article{a925ec11fb1e43d58f85d2c59ef05a4b,

title = "Reductive cyclisation 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 = "Woon, \{E C Y\} and A Dhami and Sunderland, \{P T\} and Chalkley, \{D A\} and Threadgill, \{M D\}",

year = "2006",

month = aug,

day = "1",

doi = "10.2174/157017806778559581",

language = "English",

volume = "3",

pages = "619--621",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers",

number = "8",

}

TY - JOUR

T1 - Reductive cyclisation of 2-cyanomethyl-3-nitrobenzoates

AU - Woon, E C Y

AU - Dhami, A

AU - Sunderland, P T

AU - Chalkley, D A

AU - Threadgill, M D

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

SN - 1570-1786

VL - 3

SP - 619

EP - 621

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 8

ER -

Reductive cyclisation of 2-cyanomethyl-3-nitrobenzoates

Abstract

Access to Document

Fingerprint

Cite this