Isothiourea-catalyzed synthesis of pyrrole- and indole-functionalized tetrasubstituted pyridines

Shuyue Zhang; Will Hartley; Mark David Greenhalgh; Sean Ng; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1002/cctc.202000882

Isothiourea-catalyzed synthesis of pyrrole- and indole-functionalized tetrasubstituted pyridines

Shuyue Zhang, Will Hartley, Mark David Greenhalgh, Sean Ng, Alexandra Martha Zoya Slawin, Andrew David Smith

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

Abstract

The generation of pyrrole- and indole-functionalized tetrasubstituted pyridines in a one-pot process from 2-(pyrrol-1-yl)acetic acid or 2-(indol-1-yl)acetic acid and α,β-unsaturated N-sulfonyl-ketimines is described. The process is proposed to operate via an isothiourea-catalyzed Michael addition-lactamization, followed by elimination of sulfinic acid and O-acylation to provide the final pyridine product.

Original language	English
Pages (from-to)	4522-4525
Number of pages	5
Journal	ChemCatChem
Volume	12
Issue number	18
Early online date	22 Jul 2020
DOIs	https://doi.org/10.1002/cctc.202000882
Publication status	Published - 18 Sept 2020

Keywords

Annulation
Isothiourea
Nitrogen heterocycles
Organocatalysis
Pyridines

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10.1002/cctc.202000882Licence: CC BY

Zhang_2020_ChemCatChem_Isothiourea_CC
Copyright © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 3.5 MBLicence: CC BY

CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard
ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis
Smith, A. D. (PI)
European Commission
1/10/11 → 30/06/17
Project: Standard

Isothiourea-Catalyzed Synthesis of Pyrrole- and Indole-Functionalized Tetrasubstituted Pyridines (dataset)
Smith, A. D. (Creator), Hartley, W. (Owner), Zhang, S. (Creator) & Greenhalgh, M. D. (Creator), University of St Andrews, 3 Aug 2020
DOI: 10.17630/e33b573e-516f-40dc-be0b-a623a6ac1fc3
Dataset

File

Cite this

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title = "Isothiourea-catalyzed synthesis of pyrrole- and indole-functionalized tetrasubstituted pyridines",

abstract = "The generation of pyrrole- and indole-functionalized tetrasubstituted pyridines in a one-pot process from 2-(pyrrol-1-yl)acetic acid or 2-(indol-1-yl)acetic acid and α,β-unsaturated N-sulfonyl-ketimines is described. The process is proposed to operate via an isothiourea-catalyzed Michael addition-lactamization, followed by elimination of sulfinic acid and O-acylation to provide the final pyridine product. ",

keywords = "Annulation, Isothiourea, Nitrogen heterocycles, Organocatalysis, Pyridines",

author = "Shuyue Zhang and Will Hartley and Greenhalgh, {Mark David} and Sean Ng and Slawin, {Alexandra Martha Zoya} and Smith, {Andrew David}",

note = "Funding: Engineering and Physical Sciences Research Council (Grant Number(s): EP/L016419/1); FP7 Ideas: European Research Council (Grant Number(s): 279850)",

year = "2020",

month = sep,

day = "18",

doi = "10.1002/cctc.202000882",

language = "English",

volume = "12",

pages = "4522--4525",

journal = "ChemCatChem",

issn = "1867-3880",

publisher = "John Wiley & Sons, Ltd",

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TY - JOUR

T1 - Isothiourea-catalyzed synthesis of pyrrole- and indole-functionalized tetrasubstituted pyridines

AU - Zhang, Shuyue

AU - Hartley, Will

AU - Greenhalgh, Mark David

AU - Ng, Sean

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - Funding: Engineering and Physical Sciences Research Council (Grant Number(s): EP/L016419/1); FP7 Ideas: European Research Council (Grant Number(s): 279850)

PY - 2020/9/18

Y1 - 2020/9/18

N2 - The generation of pyrrole- and indole-functionalized tetrasubstituted pyridines in a one-pot process from 2-(pyrrol-1-yl)acetic acid or 2-(indol-1-yl)acetic acid and α,β-unsaturated N-sulfonyl-ketimines is described. The process is proposed to operate via an isothiourea-catalyzed Michael addition-lactamization, followed by elimination of sulfinic acid and O-acylation to provide the final pyridine product.

AB - The generation of pyrrole- and indole-functionalized tetrasubstituted pyridines in a one-pot process from 2-(pyrrol-1-yl)acetic acid or 2-(indol-1-yl)acetic acid and α,β-unsaturated N-sulfonyl-ketimines is described. The process is proposed to operate via an isothiourea-catalyzed Michael addition-lactamization, followed by elimination of sulfinic acid and O-acylation to provide the final pyridine product.

KW - Annulation

KW - Isothiourea

KW - Nitrogen heterocycles

KW - Organocatalysis

KW - Pyridines

U2 - 10.1002/cctc.202000882

DO - 10.1002/cctc.202000882

M3 - Article

SN - 1867-3880

VL - 12

SP - 4522

EP - 4525

JO - ChemCatChem

JF - ChemCatChem

IS - 18

ER -

Isothiourea-catalyzed synthesis of pyrrole- and indole-functionalized tetrasubstituted pyridines

Abstract

Keywords

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Projects

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis

Datasets

Isothiourea-Catalyzed Synthesis of Pyrrole- and Indole-Functionalized Tetrasubstituted Pyridines (dataset)

Cite this