Ugi Reaction Followed by Intramolecular Diels–Alder Reaction and Elimination of HCl

One-Pot Approach to Arene-Fused Isoindolinones

Jianjun Huang, Xiaochen Du, Kristof Van Hecke, Erik V. Van der Eycken, Olga P. Pereshivko, Vsevolod A. Peshkov

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels–Alder reaction/HCl elimination cascade has been developed to provide rapid access to the isoindolinone framework in a diversity-oriented fashion. The scope of the process has been investigated with respect to all four components, and a comparison between the one-pot and sequential approaches is given. The possibility of a late-stage one-pot functionalization through Suzuki coupling has been explored.

Original languageEnglish
Pages (from-to)4379-4388
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number30
DOIs
Publication statusPublished - Jan 1 2017
Externally publishedYes

Fingerprint

elimination
cascades

Keywords

  • Cycloaddition
  • Diels–Alder reaction
  • Domino reactions
  • Multicomponent reactions
  • Nitrogen heterocycles
  • Ugi reaction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ugi Reaction Followed by Intramolecular Diels–Alder Reaction and Elimination of HCl : One-Pot Approach to Arene-Fused Isoindolinones. / Huang, Jianjun; Du, Xiaochen; Van Hecke, Kristof; Van der Eycken, Erik V.; Pereshivko, Olga P.; Peshkov, Vsevolod A.

In: European Journal of Organic Chemistry, Vol. 2017, No. 30, 01.01.2017, p. 4379-4388.

Research output: Contribution to journalArticle

Huang, Jianjun ; Du, Xiaochen ; Van Hecke, Kristof ; Van der Eycken, Erik V. ; Pereshivko, Olga P. ; Peshkov, Vsevolod A. / Ugi Reaction Followed by Intramolecular Diels–Alder Reaction and Elimination of HCl : One-Pot Approach to Arene-Fused Isoindolinones. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 30. pp. 4379-4388.
@article{4d878b32a06b4871ba82bd3256fe7bac,
title = "Ugi Reaction Followed by Intramolecular Diels–Alder Reaction and Elimination of HCl: One-Pot Approach to Arene-Fused Isoindolinones",
abstract = "A one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels–Alder reaction/HCl elimination cascade has been developed to provide rapid access to the isoindolinone framework in a diversity-oriented fashion. The scope of the process has been investigated with respect to all four components, and a comparison between the one-pot and sequential approaches is given. The possibility of a late-stage one-pot functionalization through Suzuki coupling has been explored.",
keywords = "Cycloaddition, Diels–Alder reaction, Domino reactions, Multicomponent reactions, Nitrogen heterocycles, Ugi reaction",
author = "Jianjun Huang and Xiaochen Du and {Van Hecke}, Kristof and {Van der Eycken}, {Erik V.} and Pereshivko, {Olga P.} and Peshkov, {Vsevolod A.}",
year = "2017",
month = "1",
day = "1",
doi = "10.1002/ejoc.201700747",
language = "English",
volume = "2017",
pages = "4379--4388",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "30",

}

TY - JOUR

T1 - Ugi Reaction Followed by Intramolecular Diels–Alder Reaction and Elimination of HCl

T2 - One-Pot Approach to Arene-Fused Isoindolinones

AU - Huang, Jianjun

AU - Du, Xiaochen

AU - Van Hecke, Kristof

AU - Van der Eycken, Erik V.

AU - Pereshivko, Olga P.

AU - Peshkov, Vsevolod A.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - A one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels–Alder reaction/HCl elimination cascade has been developed to provide rapid access to the isoindolinone framework in a diversity-oriented fashion. The scope of the process has been investigated with respect to all four components, and a comparison between the one-pot and sequential approaches is given. The possibility of a late-stage one-pot functionalization through Suzuki coupling has been explored.

AB - A one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels–Alder reaction/HCl elimination cascade has been developed to provide rapid access to the isoindolinone framework in a diversity-oriented fashion. The scope of the process has been investigated with respect to all four components, and a comparison between the one-pot and sequential approaches is given. The possibility of a late-stage one-pot functionalization through Suzuki coupling has been explored.

KW - Cycloaddition

KW - Diels–Alder reaction

KW - Domino reactions

KW - Multicomponent reactions

KW - Nitrogen heterocycles

KW - Ugi reaction

UR - http://www.scopus.com/inward/record.url?scp=85027572416&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027572416&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201700747

DO - 10.1002/ejoc.201700747

M3 - Article

VL - 2017

SP - 4379

EP - 4388

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 30

ER -