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4 article(s) from Zhang, Xiaofeng

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

Xiaofeng Zhang,
Xiaoming Ma and
Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

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Figure 1: Classification of AMYs.

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Scheme 1: Aminoester- and amino acid-based AMYs for single and double [3+2] cycloadditions.

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Scheme 2: Formation of semi-stabilized AMYs B1 from pyrrolidines.

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Scheme 3: Cyclic amine-based AMYs A3 and B1 for [3 + 2] cycloadditions.

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Scheme 4: Proposed double cycloaddition reactions involving semi-stabilized AMYs.

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Scheme 5: [3 + 2] Cycloaddition for the synthesis of trifluoromethylated pyrrolidines 9.

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Figure 2: Biologically interesting pyrrolizidines.

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Scheme 6: Double cycloadditions with glycine for the synthesis of products 10 (dr > 9:1).

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Scheme 7: Double cycloadditions with α-substituted amino acids leading to products 11 (≈8.5:1 dr).

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Scheme 8: Stereochemistry for the formation of products 10 or 11.

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Scheme 9: One-pot and stepwise double cycloadditions. Conditions: i) MeCN (0.02 M), 90 °C, 6 h; ii) then AcOH...

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Figure 3: Biologically interesting spirooxindole-pyrrolizidines.

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Scheme 10: Double cycloadditions for the synthesis of bis[spirooxindole-pyrrolizidine]s.

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Scheme 11: Mechanism for the diastereoselective synthesis of bis[spirooxindole-pyrrolizidine]s.

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Scheme 12: Stepwise synthesis of triazolobenzodiazepine 21a.

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Scheme 13: One-pot synthesis of triazolobenzodiazepines.

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Figure 4: Bioactive triazolobenzodiazepine derivatives.

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Scheme 14: One-pot synthesis of tetrahydropyrroloquinazolines.

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Scheme 15: One-pot synthesis of tetrahydropyrrolobenzodiazepines.

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Figure 5: Bioactive pyrroloquinazolines and pyrrolobenzodiazepines.

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Scheme 16: Stepwise synthesis of pyrrolo[2,1-a]isoquinolines.

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Figure 6: Bioactive pyrrolo[2,1-a]isoquinolines and hexahydropyrrolo[2,1-a]isoquinolines.

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Figure 7: Bioactive tetrahydropyrrolothiazoles.

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Scheme 17: Pseudo-four-component reaction for the synthesis of tetrahydropyrrolothiazoles 29 and 30 (>4:1 dr).

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Scheme 18: One-pot two-step synthesis of spirooxindole-pyrrolothiazoles 31 (>4:1 dr).

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Published 06 Nov 2023

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One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

Juan Lu,
Bin Yao,
Desheng Zhan,
Zhuo Sun,
Yun Ji and
Xiaofeng Zhang

Beilstein J. Org. Chem. 2022, 18, 1607–1616, doi:10.3762/bjoc.18.171

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Scheme 1: The diastereoselective synthesis of spirooxindoles through MCRs.

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Figure 1: Bioactive Spirooxindole-pyrrolothiazoles.

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Scheme 2: The synthesis of spirooxindolepyrrolothiazoles.

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Scheme 3: Four-component reaction for the synthesis of compound 5.

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Scheme 4: Proposed mechanism for the double [3 + 2] cycloadditions.

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Scheme 5: The synthesis of compound 5a with ᴅ- and ʟ-cysteine.

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Scheme 6: Two-step (process A) vs cascade (process B) synthesis of 5a. i) 1.0:1.15 of 1a/2, EtOH (0.05 M), 25...

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Figure 2: Graphical representation of the green metrics (AE, AEf, CE, RME, OE and MP) analysis for processes ...

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Figure 3: Graphical representation of the green metrics (PMI, E-factor, and SI) analysis for processes A and ...

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Published 28 Nov 2022

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Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

Xiaoming Ma,
Suzhi Meng,
Xiaofeng Zhang,
Qiang Zhang,
Shenghu Yan,
Yue Zhang and
Wei Zhang

Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106

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Figure 1: Bioactive pyrrolo[2,1-a]isoquinolines and hexahydropyrrolo[2,1-a]isoquinolines.

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Scheme 1: [3 + 2] Cycloaddition with amino esters or amino acids.

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Scheme 2: Scaffolds derived from the initial [3 + 2] adducts.

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Scheme 3: [3 + 2] Cycloaddition with amino esters or amino acids. Conditions: 1:3:4 (1.2:1:1.1), Et₃N (1.5 eq...

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Scheme 4: Synthesis of pyrrolo[2,1-a]isoquinolines 9. Reaction conditions: 5 (0.5 mmol, 1 equiv), 7 (3 equiv)...

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Scheme 5: Synthesis of pyrrolo[2,1-a]isoquinolines 11. Reaction conditions: 6 (0.5 mmol, 1 equiv), 7 (3 equiv...

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Scheme 6: Synthesis of pyrrolo[2,1-a]isoquinolines 12. Reaction conditions: 5 or 6 (0.5 mmol, 1 equiv), cinna...

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Scheme 7: Plausible mechanism for the synthesis of 9a.

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Published 04 Jun 2020

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Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

Xiaofeng Zhang,
Kenny Pham,
Shuai Liu,
Marc Legris,
Alex Muthengi,
Jerry P. Jasinski and
Wei Zhang

Beilstein J. Org. Chem. 2016, 12, 2204–2210, doi:10.3762/bjoc.12.211

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Scheme 1: Polycyclic scaffolds derived from [3 + 2] adducts 2.

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Figure 1: Heterocyclic fragments in bioactive compounds.

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Figure 2: One-pot double [3 + 2] cycloadditions and denitrogenation for product 7 under the optimized reactio...

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Figure 3: X-ray structure of 7h.

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Scheme 2: Proposed mechanism for the 2nd [3 + 2] cycloaddition and denitrogenation.

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Figure 4: [5 + 1] Annulation for tetrahydroquinazolines 1.

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Published 18 Oct 2016

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