Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

Mariateresa Giustiniano; Lisa Moni; Luca Sangaletti; Sveva Pelliccia; Andrea Basso; Ettore Novellino; Gian Cesare Tron

doi:10.1055/s-0037-1610193

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(18): 3549-3570
DOI: 10.1055/s-0037-1610193

review

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

Mariateresa Giustiniano*

^aDipartimento di Farmacia, Università degli Studi di Napoli ‘Federico II’, via D. Montesano 49, 80131 Napoli, Italy eMail: mariateresa.giustiniano@unina.it

,

Lisa Moni*

^bDipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, via Dodecaneso 31, 16146 Genova, Italy eMail: lisa.moni@unige.it

,

Luca Sangaletti

^cDipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale “A. Avogadro”, largo Donegani 2, 28100 Novara, Italy eMail: giancesare.tron@uniupo.it

,

Sveva Pelliccia

^aDipartimento di Farmacia, Università degli Studi di Napoli ‘Federico II’, via D. Montesano 49, 80131 Napoli, Italy eMail: mariateresa.giustiniano@unina.it

,

Andrea Basso

^bDipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, via Dodecaneso 31, 16146 Genova, Italy eMail: lisa.moni@unige.it

,

Ettore Novellino

^aDipartimento di Farmacia, Università degli Studi di Napoli ‘Federico II’, via D. Montesano 49, 80131 Napoli, Italy eMail: mariateresa.giustiniano@unina.it

,

Gian Cesare Tron*

^cDipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale “A. Avogadro”, largo Donegani 2, 28100 Novara, Italy eMail: giancesare.tron@uniupo.it

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Abstract

Alle Artikel dieser Rubrik

Abstract

The formation of the key short-lived intermediate nitrilium ion in the Passerini and Ugi reactions was recognized early in the discovery of these two-multicomponent transformations. Surprisingly, the idea of intramolecularly intercepting it, eluding the attack by the carboxylate, and thus interrupting the normal course of the reaction, was missed by chemists for several decades. In this review we describe, in an exhaustive manner, the reported synthetic approaches, which can be categorized as interrupted Passerini/Ugi reactions. Besides, the clear goal of this review is to show the potential of these transformations, whilst highlighting the underexplored combinations of reagents toward the identification of novel interrupted Passerini/Ugi reactions.

1 Introduction

2 The Interrupted Ugi Reaction

2.1 The Interrupting Functional Group is Present on the Amine Reactant

2.2 The Interrupting Functional Group is Present on the Isocyanide Reactant

2.3 The Interrupting Functional Group is Present on the Carbonyl Reactant

3 The Interrupted Passerini Reaction

3.1 The Interrupting Functional Group is Present on the Carbonyl Reactant

3.2 The Interrupting Functional Group is Present on the Isocyanide Reactant

4 Conclusions and Future Outlook

Key words

isocyanides - multicomponent reactions - Passerini reaction - Ugi reaction - nitrilium ions

Volltext

Referenzen

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