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Literature DB >> 25178910

Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.

Hui Li¹, Xiaoxun Li, Hao-Yuan Wang, Gabrielle N Winston-McPherson, Hao-miao Julie Geng, Ilia A Guzei, Weiping Tang.

Abstract

Various highly substituted 2,3'-diindolylmethane heterocycles were prepared from propargylic alcohols and indole nucleophiles via a transition metal-catalyzed tandem indole annulation/arylation reaction for the first time. Among the metal catalysts we examined, the most economical copper(I) catalyst provided the highest efficiency. The indole nucleophiles could also be replaced by other electron-rich arenes or alcohols.

Entities: Chemical Disease Gene

Mesh：

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Year: 2014 PMID： 25178910 PMCID： PMC4169321 DOI： 10.1039/c4cc05901h

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

25 in total

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3. Gold-catalyzed cycloisomerization reactions of 2-tosylaminophenylprop-1-yn-3-ols as a versatile approach for indole synthesis.

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Journal: Angew Chem Int Ed Engl Date: 2010-06-21 Impact factor: 15.336

4. Methyl-substituted diindolylmethanes as inhibitors of estrogen-induced growth of T47D cells and mammary tumors in rats.

Authors: A McDougal; M S Gupta; D Morrow; K Ramamoorthy; J E Lee; S H Safe
Journal: Breast Cancer Res Treat Date: 2001-03 Impact factor: 4.872

Review 5. Potential protective mechanisms of aryl hydrocarbon receptor (AHR) signaling in benign prostatic hyperplasia.

Authors: Vatsal Mehta; Chad M Vezina
Journal: Differentiation Date: 2011 Nov-Dec Impact factor: 3.880

6. Recent advances in indole syntheses: new routes for a classic target.

Authors: Rubén Vicente
Journal: Org Biomol Chem Date: 2011-07-21 Impact factor: 3.876

7. Silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-methylene-1-sulfonylindolin-3-ols.

Authors: Dewi Susanti; Fujiet Koh; Jeffrey Antonius Kusuma; Prasath Kothandaraman; Philip Wai Hong Chan
Journal: J Org Chem Date: 2012-08-27 Impact factor: 4.354

3. Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives.

Authors: Kyohei Yonekura; Mika Shinoda; Yuko Yonekura; Teruhisa Tsuchimoto
Journal: Molecules Date: 2018-04-05 Impact factor: 4.411

3 in total

Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.

Review 1. Isolation and synthesis of biologically active carbazole alkaloids.

Review 2. Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

3. Gold-catalyzed cycloisomerization reactions of 2-tosylaminophenylprop-1-yn-3-ols as a versatile approach for indole synthesis.

4. Methyl-substituted diindolylmethanes as inhibitors of estrogen-induced growth of T47D cells and mammary tumors in rats.

Review 5. Potential protective mechanisms of aryl hydrocarbon receptor (AHR) signaling in benign prostatic hyperplasia.

6. Recent advances in indole syntheses: new routes for a classic target.

7. Silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-methylene-1-sulfonylindolin-3-ols.

8. Synthesis and biological evaluation of 2,3'-diindolylmethanes as agonists of aryl hydrocarbon receptor.

Review 9. Role of the aryl hydrocarbon receptor in carcinogenesis and potential as a drug target.

Review 10. Use of natural AhR ligands as potential therapeutic modalities against inflammatory disorders.

1. Discovery of 2,3'-diindolylmethanes as a novel class of PCSK9 modulators.

2. Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

3. Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives.