Literature DB >> 22742883

Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Yuesi Fang1, Donald C Rogness, Richard C Larock, Feng Shi.   

Abstract

N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

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Year:  2012        PMID： 22742883      PMCID： PMC3407966          DOI： 10.1021/jo3011073

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  31 in total

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8.  Acridinium salt-based fluoride and acetate chromofluorescent probes: molecular insights into anion selectivity switching.

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Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

9.  A quantitative scale for the extent of conjugation of the amide bond. Amidity percentage as a chemical driving force.

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  2 in total

Review 1.  Transition-Metal-Free Activation of Amide Bond by Arynes.

Authors:  Hideto Miyabe
Journal:  Molecules       Date:  2018-08-27       Impact factor: 4.411

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  2 in total

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