“Isocyanide-less” Ugi/Intramolecular Diels-Alder reaction of 5-hydroxymethylfurfural

Research output

Abstract

The one-pot, three-step, four-component Ugi-IMDAF reaction with 5-hydroxymethylfurfural provides simple access to hydroxymethyl-substituted epoxyisoindolones in a diastereoselective and stereospecific manner. The protocol avoids the transfer or isolation of isocyanides, and the broad scope was illustrated by the synthesis of 22 different compounds bearing various substituents on the heterocyclic core.

Original languageEnglish
Pages (from-to)1578-1581
JournalTetrahedron Letters
Volume60
Issue number24
Early online date20 May 2019
DOIs
Publication statusPublished - 13 Jun 2019

Fingerprint

Bearings (structural)
Cycloaddition Reaction
Cyanides
5-hydroxymethylfurfural

Scopus subject areas

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Cite this

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title = "“Isocyanide-less” Ugi/Intramolecular Diels-Alder reaction of 5-hydroxymethylfurfural",
abstract = "The one-pot, three-step, four-component Ugi-IMDAF reaction with 5-hydroxymethylfurfural provides simple access to hydroxymethyl-substituted epoxyisoindolones in a diastereoselective and stereospecific manner. The protocol avoids the transfer or isolation of isocyanides, and the broad scope was illustrated by the synthesis of 22 different compounds bearing various substituents on the heterocyclic core.",
keywords = "5-Hydroxymethylfurfural, Diels-Alder reaction, Isocyanide-based multicomponent reaction, Ugi reaction, PRODUCTS, TRICYCLIC NITROGEN-HETEROCYCLES, UGI REACTION, SKELETAL",
author = "Pavel Golubev and Alena Pankova and Mikhail Krasavin",
year = "2019",
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day = "13",
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journal = "Tetrahedron Letters",
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AU - Golubev, Pavel

AU - Pankova, Alena

AU - Krasavin, Mikhail

PY - 2019/6/13

Y1 - 2019/6/13

N2 - The one-pot, three-step, four-component Ugi-IMDAF reaction with 5-hydroxymethylfurfural provides simple access to hydroxymethyl-substituted epoxyisoindolones in a diastereoselective and stereospecific manner. The protocol avoids the transfer or isolation of isocyanides, and the broad scope was illustrated by the synthesis of 22 different compounds bearing various substituents on the heterocyclic core.

AB - The one-pot, three-step, four-component Ugi-IMDAF reaction with 5-hydroxymethylfurfural provides simple access to hydroxymethyl-substituted epoxyisoindolones in a diastereoselective and stereospecific manner. The protocol avoids the transfer or isolation of isocyanides, and the broad scope was illustrated by the synthesis of 22 different compounds bearing various substituents on the heterocyclic core.

KW - 5-Hydroxymethylfurfural

KW - Diels-Alder reaction

KW - Isocyanide-based multicomponent reaction

KW - Ugi reaction

KW - PRODUCTS

KW - TRICYCLIC NITROGEN-HETEROCYCLES

KW - UGI REACTION

KW - SKELETAL

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DO - 10.1016/j.tetlet.2019.05.018

M3 - Article

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SP - 1578

EP - 1581

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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