A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

Alan M. Jones; Stephen Patterson; Magali Myriam Lorion; Alexandra Martha Zoya Slawin; Nicholas James Westwood

doi:10.1039/C6OB01566B

A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

Alan M. Jones, Stephen Patterson, Magali Myriam Lorion, Alexandra Martha Zoya Slawin, Nicholas James Westwood

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

Abstract

Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.

Original language	English
Pages (from-to)	8998-9011
Number of pages	14
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	38
Early online date	30 Aug 2016
DOIs	https://doi.org/10.1039/C6OB01566B
Publication status	Published - 14 Oct 2016

Keywords

Rearrangement
Medium-sized ring
Core-switching
Diversity-Oriented Synthesis
Pyrrolo[2,3-b]quinoline
Diazocino[1,2-a]indolinone

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10.1039/C6OB01566B

Westwood_2016_OBC_CoreSwitching_AAM
Copyright 2016 the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1039/C6OB01566B
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Cite this

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title = "A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones",

abstract = "Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.",

keywords = "Rearrangement, Medium-sized ring, Core-switching, Diversity-Oriented Synthesis, Pyrrolo[2,3-b]quinoline, Diazocino[1,2-a]indolinone",

author = "Jones, {Alan M.} and Stephen Patterson and Lorion, {Magali Myriam} and Slawin, {Alexandra Martha Zoya} and Westwood, {Nicholas James}",

note = "The authors gratefully acknowledge the Royal Society (NJW held a URF at the time this work was done), and the BBSRC for PhD funding through the Doctoral Training Scheme (AMJ). ",

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doi = "10.1039/C6OB01566B",

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AU - Jones, Alan M.

AU - Patterson, Stephen

AU - Lorion, Magali Myriam

AU - Slawin, Alexandra Martha Zoya

AU - Westwood, Nicholas James

N1 - The authors gratefully acknowledge the Royal Society (NJW held a URF at the time this work was done), and the BBSRC for PhD funding through the Doctoral Training Scheme (AMJ).

PY - 2016/10/14

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N2 - Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.

AB - Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.

KW - Rearrangement

KW - Medium-sized ring

KW - Core-switching

KW - Diversity-Oriented Synthesis

KW - Pyrrolo[2,3-b]quinoline

KW - Diazocino[1,2-a]indolinone

UR - http://www.rsc.org/suppdata/c6/ob/c6ob01566b/c6ob01566b1.pdf

U2 - 10.1039/C6OB01566B

DO - 10.1039/C6OB01566B

M3 - Article

SN - 1477-0520

VL - 14

SP - 8998

EP - 9011

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 38

ER -

A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

Abstract

Keywords

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