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Review
. 2018 Sep 4;23(9):2255.
doi: 10.3390/molecules23092255.

Gold Catalyzed Multicomponent Reactions beyond A³ Coupling

Renso Visbal  1 , Sara Graus  2 , Raquel P Herrera  3 , M Concepción Gimeno  4
Affiliations
Review

Gold Catalyzed Multicomponent Reactions beyond A³ Coupling

Renso Visbal et al. Molecules. .

Abstract

The preparation of complex architectures has inspired the search for new methods and new processes in organic synthesis. Multicomponent reactions have become an interesting approach to achieve such molecular diversity and complexity. This review intends to illustrate important gold-catalyzed examples for the past ten years leading to interesting skeletons involved in biologically active compounds.

Keywords: 1,4-dihydropyridines; 3,4-dihydropyrimidin-2(1H)-ones; butenolides; catalysis; ethers; gold; multicomponent reactions; oxazoles; pyridines; spirocycles; thiazolo-quinolines; β-alkoxyketones.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structural cores described in this review and synthesized by means of gold-catalyzed MCRs.
Scheme 1
Scheme 1
Biginelli reaction catalyzed by Au nanorods.
Figure 2
Figure 2
Biologically active 1,4-DHPs.
Scheme 2
Scheme 2
Au(I)-catalyzed multicomponent synthesis of 1,4-dihydropyridines 8.
Scheme 3
Scheme 3
Proposed catalytic cycle for the synthesis of 8aa.
Figure 3
Figure 3
Biologically active pyridine derivatives.
Scheme 4
Scheme 4
Multicomponent synthesis of highly substituted pyridines 13 and 15.
Scheme 5
Scheme 5
Proposed stepwise mechanism for the preparation of pyridines 13.
Scheme 6
Scheme 6
Structural variations in the alkyne compound 21 (salen: N,N′-ethylenebis(salicylimine)).
Scheme 7
Scheme 7
Structural variations in the acyl chlorides 20.
Scheme 8
Scheme 8
Structural variations in the imines 19.
Scheme 9
Scheme 9
Proposed mechanism for the gold-catalyzed formation of oxazoles XI.
Figure 4
Figure 4
Biologically active β-alkoxy ketones.
Scheme 10
Scheme 10
Gold(I)-catalyzed multicomponent synthesis of β-alkoxyketones 26.
Scheme 11
Scheme 11
Previously proposed mechanism for Au(I)-catalyzed synthesis of β-alkoxyketones 26 via oxyauration of hemiacetals.
Scheme 12
Scheme 12
Use of water as nucleophile in the hydroxyarylation process (TFAHN: trifluoroacetamide; TsN: toluensulfonamide).
Scheme 13
Scheme 13
Plausible mechanism of the hydroxyarylation process.
Scheme 14
Scheme 14
Synthesis of thiazoloquinolines 46.
Figure 5
Figure 5
Spirotryprostatins A and B [89], pteropodine and isopteropodine [90], rhynchophylline [91] and formosanine [92].
Scheme 15
Scheme 15
HAuCl4·3H2O catalyzed multicomponent synthesis of spirocycles 50 and 51.
Scheme 16
Scheme 16
HAuCl4·3H2O catalyzed multicomponent synthesis of spirocycles 53.
Scheme 17
Scheme 17
Plausible pathways for the synthesis of spirooxindole 50a.
Scheme 18
Scheme 18
Gold-catalyzed multicomponent synthesis of butenolides 57.
Scheme 19
Scheme 19
Gold-catalyzed tandem process for the synthesis of butenolides 59.
Scheme 20
Scheme 20
Catalytic cycle for the synthesis of butenolides 57 and 59.
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References

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