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. 2009;15(6):1300-8.
doi: 10.1002/chem.200802140.

Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds

James D Sunderhaus  1 , Stephen F Martin
Affiliations

Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds

James D Sunderhaus et al. Chemistry. 2009.

Abstract

The sequencing of multicomponent reactions (MCRs) and subsequent cyclization reactions is a powerful stratagem for the rapid synthesis of diverse heterocyclic scaffolds. The optimal MCR is sufficiently flexible that it can be employed to generate adducts bearing a variety of functional groups that may then be selectively paired to enable different cyclization manifolds, thereby leading to a diverse collection of products. The growing interest in diversity-oriented synthesis has led to increased attention to this paradigm for library synthesis, which has inspired many advances in the design and implementation of MCRs for the construction of diverse heterocyclic scaffolds.

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Figures

Scheme 1
Scheme 1
Sequencing of MCRs with post condensation cyclizations to generate diverse scaffolds.
Scheme 2
Scheme 2
An overview of the U-4CR post condensation cyclizations.
Scheme 3
Scheme 3
Sequential Ugi-Smiles/RCM or Ugi-Smiles/Heck
Scheme 4
Scheme 4
Schreiber’s use of the Petasis 3CR for the synthesis of 15 distinct heterocyclic scaffolds.
Scheme 5
Scheme 5
Diverse heterocyclic scaffolds accessible by the van Leusen 3CR.
Scheme 6
Scheme 6
Sequential AAD/Pauson-Khand and AAD/Alder-ene reactions.
Scheme 7
Scheme 7
Sequential AAD/Heck reaction.
Scheme 8
Scheme 8
α,γ-Difunctionalization reaction of β-ketoamides and its application to the synthesis of spiroheterocycles.
Scheme 9
Scheme 9
A 4CR approach to the synthesis of diverse triazinane diones.
Scheme 10
Scheme 10
Sequential Mannich-type 4CR/RCM/Dieckmann Cyclization.
Scheme 11
Scheme 11
Sequential Mannich-type 4CR/RCM/Heck Cyclization.
Scheme 12
Scheme 12
Sequential Mannich-type 4CR/Cycloaddition.
Scheme 13
Scheme 13
Application of the Mannich-type 4CR to the synthesis of (±)-roelactamine.
See this image and copyright information in PMC

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