Amide bond formation via the rearrangement of nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides

Mhairi Boyle; Keith Livingstone; Martyn C. Henry; Jessica M. L. Elwood; J. Daniel Lopez Fernandez; Craig Jamieson

doi:10.1021/acs.orglett.1c03993

Amide bond formation via the rearrangement of nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides

Mhairi Boyle, Keith Livingstone, Martyn C. Henry, Jessica M. L. Elwood, J. Daniel Lopez Fernandez, Craig Jamieson

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

12 Citations (Scopus)

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Abstract

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

Original language	English
Pages (from-to)	334-338
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	1
Early online date	29 Dec 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c03993
Publication status	Published - 14 Jan 2022

Keywords

amide bond formation
rearrangement of nitrile imines
N-2-nitrophenyl hydrazonyl bromides

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10.1021/acs.orglett.1c03993Licence: CC BY 4.0

Boyle-etal-OL-2021-Amide-bond-formation-via-the-rearrangement-of-nitrile-imines-derived-from-N-2-nitrophenyl-hydrazonyl-bromidesFinal published version, 1.63 MBLicence: CC BY 4.0

Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation
Kerr, W. (Principal Investigator), Brown, C. (Co-investigator), Florence, A. (Co-investigator), Jamieson, C. (Co-investigator), Johnston, B. (Co-investigator), Murphy, J. (Co-investigator), Palmer, D. (Co-investigator) & Tomkinson, N. (Co-investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/01/19 → 30/09/24
Project: Research

Cite this

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title = "Amide bond formation via the rearrangement of nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides",

abstract = "We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.",

keywords = "amide bond formation, rearrangement of nitrile imines, N-2-nitrophenyl hydrazonyl bromides",

author = "Mhairi Boyle and Keith Livingstone and Henry, {Martyn C.} and Elwood, {Jessica M. L.} and {Lopez Fernandez}, {J. Daniel} and Craig Jamieson",

year = "2022",

month = jan,

day = "14",

doi = "10.1021/acs.orglett.1c03993",

language = "English",

volume = "24",

pages = "334--338",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Amide bond formation via the rearrangement of nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides

AU - Boyle, Mhairi

AU - Livingstone, Keith

AU - Henry, Martyn C.

AU - Elwood, Jessica M. L.

AU - Lopez Fernandez, J. Daniel

AU - Jamieson, Craig

PY - 2022/1/14

Y1 - 2022/1/14

N2 - We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

AB - We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

KW - amide bond formation

KW - rearrangement of nitrile imines

KW - N-2-nitrophenyl hydrazonyl bromides

U2 - 10.1021/acs.orglett.1c03993

DO - 10.1021/acs.orglett.1c03993

M3 - Letter

SN - 1523-7060

VL - 24

SP - 334

EP - 338

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Amide bond formation via the rearrangement of nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides

Abstract

Keywords

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Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation

Cite this