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3 article(s) from Rivera, Daniel G

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

Gerardo M. Ojeda,
Prabhat Ranjan,
Pavel Fedoseev,
Lisandra Amable,
Upendra K. Sharma,
Daniel G. Rivera and
Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

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Figure 1: Bioactive molecules containing a tetrazole, pyridone or isoquinolone ring.

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Scheme 1: Approaches for the synthesis of tetrazoles and isoquinolones and their interplay as designed in thi...

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Scheme 2: Scope of the Ugi-azide-4CR/deprotection/acylation sequence. Ugi-azide-4CR conducted at the 2.0 mmol...

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Scheme 3: Influence of substituents R and R² on the reaction outcome. For compounds 4k–m the overall yield in...

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Scheme 4: Influence of the alkyne and R¹ substituent on the reaction outcome.

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Scheme 5: Scope of acrylic, heterocyclic and ring-fused N-acylaminomethyl tetrazole substrates.

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Scheme 6: Proposed reaction mechanism using substrates 1a and 3a.

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Published 16 Oct 2019

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Steroid diversification by multicomponent reactions

Leslie Reguera,
Cecilia I. Attorresi,
Javier A. Ramírez and
Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

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Figure 1: Structures of natural steroids of A) animal and B) plant origin.

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Scheme 1: Synthesis of a steroidal β-lactam by Ugi reaction of a cholanic aldehyde [14].

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Scheme 2: Synthetic route to steroidal 2,5-diketopiperazines based on a diastereoselective Ugi-4CR with an an...

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Scheme 3: Multicomponent synthesis of a heterocycle–steroid hybrid using a ketosteroid as carbonyl component [18]....

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Scheme 4: Synthesis of peptidomimetic–steroid hybrids using the Ugi-4CR with spirostanic amines and carboxyli...

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Scheme 5: Synthesis of azasteroids using the Ugi-4CR with androstanic and pregnanic carboxylic acids [22].

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Figure 2: Ugi-4CR-derived library of androstanic azasteroids with diverse substitution patterns at the phenyl...

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Scheme 6: Synthesis of 4-azacholestanes by an intramolecular Ugi-4C-3R [26].

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Scheme 7: Synthesis of amino acid–steroid hybrid by multiple Ugi-4CR using steroidal isocyanides [29].

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Scheme 8: Synthesis of ecdysteroid derivatives by Ugi-4CR using a steroidal isocyanide [30].

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Scheme 9: Stereoselective multicomponent synthesis of a steroid–tetrahydropyridine hybrid using a chiral bifu...

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Scheme 10: Pd(II)-catalyzed three-component reaction with an alkynyl seco-cholestane [34].

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Scheme 11: Multicomponent synthesis of steroid–thiazole hybrids from a steroidal ketone [36].

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Scheme 12: Synthesis of cholanic pseudo-peptide derivatives by novel MCRs based on the reactivity of ynamide [37,38].

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Scheme 13: Synthesis of steroid-fused pyrimidines and pyrimidones using the Biginelli-3CR [39,42,43].

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Scheme 14: Synthesis of steroidal pyridopyrimidines by a reaction sequence comprising a 4CR followed by a post...

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Scheme 15: Synthesis of steroid-fused pyrimidines by MCR of 2-hydroxymethylene-3-ketosteroids [46].

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Scheme 16: Synthesis of steroid-fused naphthoquinolines by the Kozlov–Wang MCR using ketosteroids [50,51].

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Scheme 17: Conjugation of steroids to carbohydrates and peptides by the Ugi-4CR [62,63].

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Scheme 18: Solid-phase multicomponent conjugation of peptides to steroids by the Ugi-4CR [64].

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Scheme 19: Solid-phase multicomponent conjugation of peptides to steroids by the Petasis-3CR [68].

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Scheme 20: Synthesis of steroidal macrobicycles (cages) by multiple multicomponent macrocyclizations based on ...

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Scheme 21: One-pot synthesis of steroidal cages by double Ugi-4CR-based macrocyclizations [76].

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Review

Published 06 Jun 2019

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Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis

Alexander F. de la Torre,
Gabriel S. Scatena,
Oscar Valdés,
Daniel G. Rivera and
Márcio W. Paixão

Beilstein J. Org. Chem. 2019, 15, 1210–1216, doi:10.3762/bjoc.15.118

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Scheme 1: Schematic synthesis of polyfurfulyl alcohol (PFA) incorporating a prolyl peptide catalyst. AA: Amin...

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Scheme 2: Utilization of the Ugi four-component reaction (Ugi-4CR) for the synthesis of prolyl pseudo-peptide...

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Figure 1: Analysis of the continuous-flow catalytic system producing γ-nitroaldehyde 5 with PFA-supported cat...

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Published 04 Jun 2019

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