Coupling Isocyanide-Based
Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution
Processes

Luca Banfi; Renata Riva; Andrea Basso

doi:10.1055/s-0029-1218527

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Synlett 2010(1): 23-41
DOI: 10.1055/s-0029-1218527

ACCOUNT

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Luca Banfi*, Renata Riva*, Andrea Basso
Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy
Fax: +39(010)3536118; e-Mail: banfi@chimica.unige.it; e-Mail: riva@chimica.unige.it;

Further Information

Publication History

Received 17 July 2009
Publication Date:
30 November 2009 (online)

Abstract
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Abstract

This account summarizes the results of studies carried out by the authors during the last 10 years aimed at expanding the utility of the venerable Passerini and Ugi reactions. Particular emphasis is given to efforts that focus on coupling these processes with post-condensation, intramolecular, aliphatic nucleophilic substitution and acyl nucleophilic substitution reactions. The methodologies developed in these investigations serve as the basis for short sequences for the preparation of a diverse number of interesting drug-like structures.

1 Introduction

2 Aliphatic Nucleophilic Substitution

2.1 Two Additional Functions: Mitsunobu or Mitsunobu-like Reactions

2.2 One Additional Function: Ketopiperazines, β-Lactams and More

2.3 One Additional Function: S_N2′ Reactions

3 Nucleophilic Acyl Substitutions: Acyl Migrations

3.1 Oxygen → Nitrogen Migration after Passerini (PADAM)

3.2 Nitrogen → Oxygen Migration after Ugi (UNOAM)

4 Nucleophilic Acyl Substitutions: Lactonization or Lactamization

4.1 Two Additional Functions

4.2 One Additional Function

5 Conclusions

Key words

multicomponent reactions - heterocycles - combinatorial chemistry - Mitsunobu reaction - acylations

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