An amine template strategy to construct successive C–C bonds: synthesis of benzo[<i>h</i>]quinolines by a deaminative ring contraction cascade-Reference-Cited by-同舟云学术

An amine template strategy to construct successive C–C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade

Published:2022 Issue:7 Volume:20 Page:1379-1385
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

McFadden Timothy Patrick¹^ORCID,Nwachukwu Chideraa Iheanyi¹^ORCID,Roberts Andrew George¹^ORCID

Affiliation:

1. Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA

Abstract

We report a strategy to build, cyclize, and excise nitrogen from tertiary amines for the synthesis of polyheterocyclic aromatics. A developed deaminative ring contraction cascade reaction is useful for the synthesis of substituted benzoquinolines.

Funder

University of Utah

American Chemical Society Petroleum Research Fund

National Institutes of Health

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/OB/D1OB02245H

Reference74 articles.

1. Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

2. The art of total synthesis through cascade reactions

3. A Case Study in Biomimetic Total Synthesis: Polyolefin Carbocyclizations to Terpenes and Steroids

4. CCCCXXIII.—Degradation of quaternary ammonium salts. Part I

5. S. H.Pine , The Base-Promoted Rearrangements of Quaternary Ammonium Salts , John Wiley & Sons, Inc. , Hoboken, NJ, USA , 2011 , p. 403

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