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2 article(s) from Ma, Xiaoming

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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Graphical Abstract

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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Perspective

Published 06 Nov 2023

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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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Graphical Abstract

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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