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5 article(s) from Andrade, Carlos Kleber Z.

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

Luan A. Martinho and
Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

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Figure 1: Selected examples of commercial drugs containing the imidazo[1,2-a]pyridine core [13].

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Figure 2: Examples of application of HPW as catalyst in the synthesis of heterocyclic compounds through multi...

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Scheme 1: a) Reported phosphomolybdic acid-catalyzed synthesis of imidazo[1,2-a]pyridines via GBB-3CR. b) Att...

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Scheme 2: Substrate scope of the HPW-catalyzed GBB reactions using a range of aromatic/heteroaromatic aldehyd...

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Scheme 3: Substrate scope of the HPW-catalyzed GBB reaction using aliphatic aldehydes. Reaction conditions: 2...

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Scheme 4: Unsuccessful substrates for the HPW-catalyzed GBB-3CR for the synthesis of imidazo[1,2-a]pyridines.

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Scheme 5: 10-Fold scale-up of the HPW-catalyzed GBB reaction (5.0 mmol) between 2-aminopyridine (1a), 4-nitro...

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Scheme 6: Plausible reaction mechanism for the HPW-catalyzed GBB reaction.

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Full Research Paper

Published 19 Mar 2024

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Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

Angélica de Fátima S. Barreto and
Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

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Scheme 1: Comparison between a normal sequential reaction and an MCR.

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Scheme 2: Synthesis of tetrazoles and hydantoinimide derivatives by consecutive Ugi reactions [17].

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Scheme 3: Synthesis of tetrazole-ketopiperazines by two consecutive Ugi reactions [19].

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Scheme 4: Synthesis of acylhydrazino bis(1,5-disubstituted tetrazoles) through two hydrazine-Ugi-azide reacti...

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Scheme 5: Synthesis of substituted α-aminomethyltetrazoles through two consecutive Ugi reactions (U-4CR and U...

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Scheme 6: Synthesis of tetrazole peptidomimetics by direct use of amino acids in two consecutive Ugi reaction...

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Scheme 7: One-pot 8CR based on 3 sequential IMCRs [25].

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Scheme 8: Combination of IMCRs for the synthesis of substituted 2H-imidazolines [25].

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Scheme 9: 6CR involving a tandem combination of Groebke–Blackburn–Bienaymé and Ugi reaction for the synthesis...

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Scheme 10: 5CR involving a tandem combination of Groebke–Blackburn–Bienaymé and Passerini reaction for the syn...

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Scheme 11: Synthesis of tubugis via three consecutive IMCRs [27].

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Scheme 12: Synthesis of telaprevir through consecutive IMCRs [28].

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Scheme 13: Another synthesis of telaprevir through consecutive IMCRs [29].

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Scheme 14: a) Synthetic sequence for accessing diverse macrocycles containing the tetrazole nucleus by the uni...

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Scheme 15: a) Synthetic sequence for the tetrazolic macrocyclic depsipeptides using a combination of two IMCRs...

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Scheme 16: Synthesis of cyclic pentapeptoids by consecutive Ugi reactions [32].

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Scheme 17: Synthesis of a cyclic pentapeptoid by consecutive Ugi reactions [32].

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Scheme 18: MW-mediated synthesis of a cyclopeptoid by consecutive Ugi reactions [33].

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Scheme 19: Synthesis of six cyclic pentadepsipeptoids via consecutive isocyanide-based IMCRs [34].

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Scheme 20: Microwave-mediated synthesis of a cyclic heptapeptoid through four consecutive IMCRs [35].

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Scheme 21: Macrocyclization of bifunctional building blocks containing diacid/diisonitrile and diamine/diisoni...

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Scheme 22: Synthesis of steroid-biaryl ether hybrid macrocycles by MiBs [38].

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Scheme 23: Synthesis of biaryl ether-containing macrocycles by MiBs [39].

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Scheme 24: Synthesis of natural product-inspired biaryl ether-cyclopeptoid macrocycles [40].

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Scheme 25: Synthesis of cholane-based hybrid macrolactams by MiBs [41].

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Scheme 26: Synthesis of macrocyclic oligoimine-based DCL using the Ugi-4CR-based quenching approach [42].

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Scheme 27: Dye-modified and photoswitchable macrocycles by MiBs [43].

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Scheme 28: Synthesis of nonsymmetric cryptands by two sequential double Ugi-4CR-based macrocyclizations [44].

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Scheme 29: Synthesis of steroid–aryl hybrid cages by sequential 2- and 3-fold Ugi-4CR-based macrocyclizations [46]....

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Scheme 30: Ugi-MiBs approach towards natural product-like macrocycles [47].

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Scheme 31: a) Bidirectional macrocyclization of peptides by double Ugi reaction. b) Ugi-4CR for the generation...

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Scheme 32: MiBs based on the Passerini-3CR for the synthesis of macrolactones [49].

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Scheme 33: Template-driven approach for the synthesis of macrotricycles 170 [50].

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Published 15 Apr 2019

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Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles

Angélica de Fátima S. Barreto,
Veronica Alves dos Santos and
Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2017, 13, 2596–2602, doi:10.3762/bjoc.13.256

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Figure 1: Tetrazole-containing drugs.

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Scheme 1: Synthesis of acylhydrazino bis(1,5-disubstituted tetrazoles) through two hydrazino-Ugi-azide reacti...

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Scheme 2: Synthesis of hydrazides 2a–c. Reagents and conditions: (i) N₂H₄·H₂O, EtOH, reflux, 2–3 h; (ii) CH₃I...

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Scheme 3: Synthesis of acylhydrazino 1,5-disubstituted tetrazoles 10a–h through multicomponent reactions invo...

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Scheme 4: Synthesis of acylhydrazino 1,5-disubstituted tetrazoles 10i–m through multicomponent reactions invo...

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Scheme 5: Synthesis of acylhydrazino bis(1,5-disubstituted tetrazoles) 12a–d.

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Scheme 6: Possible postmodification reactions of the acylhydrazino bis(1,5-disubstituted tetrazoles) 12a–d.

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Published 05 Dec 2017

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Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

Angélica de Fátima S. Barreto,
Veronica Alves dos Santos and
Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2016, 12, 2865–2872, doi:10.3762/bjoc.12.285

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Figure 1: Structural features of (a) peptide, (b) peptoid, (c) peptomer, (d) azapeptide, (e) azapeptoid, (f) ...

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Figure 2: Some biologically active peptoids.

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Figure 3: Biologically active hydrazinopeptides and representation of the hydrazino turn.

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Figure 4: General structure of the acylhydrazino-peptomers synthesized in this study.

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Scheme 1: Retrosynthetic analysis.

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Scheme 2: Synthesis of hydrazides 3a–c. Reagents and conditions: (i) CH₃I, NaHCO₃, DMF, rt, 46 h; (ii) N₂H₄^.H₂...

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Scheme 3: Synthesis of acylhydrazino-peptomers 11a–f.

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Scheme 4: Synthesis of acylhydrazino-peptomers 14a,b.

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Scheme 5: Synthesis of acylhydrazino-peptomers 15a–c.

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Published 27 Dec 2016

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Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

Angélica de Fátima S. Barreto,
Otilie E. Vercillo,
Ludger A. Wessjohann and
Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2014, 10, 1017–1022, doi:10.3762/bjoc.10.101

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Figure 1: Sansalvamide A (1) and its depsipeptoid analogues (2).

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Figure 2: Generic structures of (a) peptide, (b) peptoid, (c) depsipeptide and (d) depsipeptoid.

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Figure 3: Structures of six pentadepsipeptoid analogues of San A.

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Scheme 1: Retrosynthetic analysis of the cyclic depsipeptoids.

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Scheme 2: Synthesis of acyclic depsipeptoids 11a,b.

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Scheme 3: Synthesis of macrocycles 2a-f.

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Letter

Published 05 May 2014

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