Literature DB >> 33299258

Superacid-promoted synthesis of quinoline derivatives.

Hein Vuong1, Michael R Stentzel1, Douglas A Klumpp1.   

Abstract

A series of vinylogous imines have been prepared from anilines and cinnamaldehydes. These substrates react in superacidic media to provide quinolines and related compounds. A mechanism for the conversion is proposed which involves the cyclization of dicationic superelectrophilic intermediates. Aromatization of the quinoline ring is thought to occur by superacid-promoted elimination of benzene.

Entities:  

Keywords:  Cyclization; Heterocycle; Quinoline; Superacid; Superelectrophile

Year:  2020        PMID： 33299258      PMCID： PMC7720793          DOI： 10.1016/j.tetlet.2020.151630

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  14 in total

1.  Superelectrophiles: charge-charge repulsive effects.

Authors:  Douglas A Klumpp
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

Review 2.  Recent advances in research of natural and synthetic bioactive quinolines.

Authors:  Po-Yee Chung; Zhao-Xiang Bian; Ho-Yuen Pun; Dessy Chan; Albert Sun-Chi Chan; Chung-Hin Chui; Johnny Cheuk-On Tang; Kim-Hung Lam
Journal:  Future Med Chem       Date:  2015       Impact factor: 3.808

3.  Quinolines block every step of malaria heme crystal growth.

Authors:  David J Sullivan
Journal:  Proc Natl Acad Sci U S A       Date:  2017-07-10       Impact factor: 11.205

Review 4.  Quinoline hybrids and their antiplasmodial and antimalarial activities.

Authors:  Yuan-Qiang Hu; Chuan Gao; Shu Zhang; Lei Xu; Zhi Xu; Lian-Shun Feng; Xiang Wu; Feng Zhao
Journal:  Eur J Med Chem       Date:  2017-07-27       Impact factor: 6.514

5.  A versatile methodology for the synthesis of alpha,beta-unsaturated 3-iminophosphines.

Authors:  Andrew R Shaffer; Joseph A R Schmidt
Journal:  Chemistry       Date:  2009-03-02       Impact factor: 5.236

Review 6.  Medicinal chemistry of quinolines as emerging anti-inflammatory agents: an overview.

Authors:  S Mukherjee; M Pal
Journal:  Curr Med Chem       Date:  2013       Impact factor: 4.530

7.  Preparation of aza-polycyclic aromatic compounds via superelectrophilic cyclizations.

Authors:  Ang Li; Thomas M Gilbert; Douglas A Klumpp
Journal:  J Org Chem       Date:  2008-04-01       Impact factor: 4.354

8.  Ring closing and opening reactions leading to aza-polycyclic aromatic compounds.

Authors:  Anila Kethe; Ang Li; Douglas A Klumpp
Journal:  Tetrahedron       Date:  2012-04-20       Impact factor: 2.457

9.  Charge migration in dicationic electrophiles and its application to the synthesis of aza-polycyclic aromatic compounds.

Authors:  Ang Li; Patrick J Kindelin; Douglas A Klumpp
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005

10.  Antileishmanial, antimicrobial and antifungal activities of some new aryl azomethines.

Authors:  Yasser M S A Al-Kahraman; Hassan M F Madkour; Dildar Ali; Masoom Yasinzai
Journal:  Molecules       Date:  2010-01-28       Impact factor: 4.411
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