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Literature DB >> 29022706

Understanding and Interrupting the Fischer Azaindolization Reaction.

Bryan J Simmons¹, Marie Hoffmann¹, Pier Alexandre Champagne¹, Elias Picazo¹, Katsuya Yamakawa¹, Lucas A Morrill¹, K N Houk¹, Neil K Garg¹.

Abstract

Experimental and computational studies pertaining to the Fischer azaindolization reaction are reported. These studies explain why pyridylhydrazines are poorly reactive in Fischer indolization reactions, in addition to the origin of hydrazine substituent effects. Additionally, an interrupted variant of Fischer azaindolization methodology is disclosed, which provides a synthetic entryway into fused azaindoline scaffolds.

Entities: Chemical Disease Gene

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Year: 2017 PMID： 29022706 PMCID： PMC5726400 DOI： 10.1021/jacs.7b07518

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

16 in total

Review 1. Practical methodologies for the synthesis of indoles.

Authors: Guy R Humphrey; Jeffrey T Kuethe
Journal: Chem Rev Date: 2006-07 Impact factor: 60.622

2. Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids--a generalized approach.

Authors: Sebastian Krüger; Tanja Gaich
Journal: Angew Chem Int Ed Engl Date: 2014-10-24 Impact factor: 15.336

3. Intramolecular Fischer Indole Synthesis for the Direct Synthesis of 3,4-Fused Tricyclic Indole and Application to the Total Synthesis of (-)-Aurantioclavine.

Authors: Jun Park; Dong-Hyun Kim; Tapas Das; Cheon-Gyu Cho
Journal: Org Lett Date: 2016-09-19 Impact factor: 6.005

Understanding and Interrupting the Fischer Azaindolization Reaction.

Review 1. Practical methodologies for the synthesis of indoles.

2. Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids--a generalized approach.

3. Intramolecular Fischer Indole Synthesis for the Direct Synthesis of 3,4-Fused Tricyclic Indole and Application to the Total Synthesis of (-)-Aurantioclavine.

4. Two-step route to indoles and analogues from haloarenes: a variation on the Fischer indole synthesis.

5. Total Synthesis of Scholarisine K and Alstolactine A.

6. Synthesis of 4- and 6-azaindoles via the Fischer reaction.

7. Asymmetric Synthesis of Tetracyclic Pyrroloindolines and Constrained Tryptamines by a Switchable Cascade Reaction.

8. Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia.

Review 9. The azaindole framework in the design of kinase inhibitors.

10. Total synthesis of the akuammiline alkaloid picrinine.

1. Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.