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Synlett 2010(1): 23-41
DOI: 10.1055/s-0029-1218527
DOI: 10.1055/s-0029-1218527
ACCOUNT
© Georg Thieme Verlag
Stuttgart ˙ New York
Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes
Weitere Informationen
Received
17 July 2009
Publikationsdatum:
30. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
30. November 2009 (online)
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: SN2′ 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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