Nitrile N-Oxides and Nitrile Imines as New Fuels for the Discovery of Novel Isocyanide-Based Multicomponent Reactions

Mariateresa Giustiniano; Ettore Novellino; Gian Cesare Tron

doi:10.1055/s-0035-1561672

Synthesis, Table of Contents

Synthesis 2016; 48(17): 2721-2731
DOI: 10.1055/s-0035-1561672

short review

Nitrile N-Oxides and Nitrile Imines as New Fuels for the Discovery of Novel Isocyanide-Based Multicomponent Reactions

Mariateresa Giustiniano*

^aDipartimento di Farmacia, Università degli Studi di Napoli ‘Federico II’, Via D. Montesano 49, 80131, Napoli, Italy

,

Ettore Novellino

^aDipartimento di Farmacia, Università degli Studi di Napoli ‘Federico II’, Via D. Montesano 49, 80131, Napoli, Italy

,

Gian Cesare Tron*

^bDipartimento di Scienza del Farmaco, Università degli Studi del Piemonte Orientale ‘A. Avogadro’, Largo Donegani 2, 28100 Novara, Italy Email: mariateresa.giustiniano@unina.it Email: giancesare.tron@uniupo.it

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Abstract

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Abstract

With this short review we would like to describe our work on isocyanide-mediated multicomponent reactions using the 1,3-dipolar species nitrile N-oxides and nitrile imines as electrophilic inputs. Our goal is to show the potentiality of these transformations, elucidate the mechanisms of the reactions, demonstrate the versatility, and highlight the potentiality of this chemistry.

1 Introduction

2 (Z)-Chloroximes as Electrophilic Partners for Isocyanides

2.1 Precedents for the Reaction Between Nitrile N-Oxides and Isocyanides

2.2 Reaction between (Z)-Chloroximes, Isocyanides, and Carboxylic Acids (or Amines)

2.3 The Use of Other Nucleophiles as the Third Partner

2.4 General Mechanism

3 Nitrile Imines as Electrophilic Partners for Isocyanides

4 Conclusions and Future Outlook

Key words

isocyanides - multicomponent reactions - Passerini reaction - nitrile N-oxides - cycloaddition reactions - chloroximes - nitrile imines

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References

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