Literature DB >> 24143035

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

Anila Kethe1, Ang Li, Douglas A Klumpp.   

Abstract

A series of functionalized aza-polycyclic aromatic compounds were prepared by a superacid-promoted ring closing and opening reaction cascade. A reaction mechanism is proposed, which involves reactive dicationic intermediates. A key step in the conversions involves ipso protonation of an aryl group and elimination of an alkyl phenyl group.

Entities:  

Keywords:  Aza-polycyclic aromatic compounds; Condensation; Dication; Heterocycle; Superacid

Year:  2012        PMID： 24143035      PMCID： PMC3797622          DOI： 10.1016/j.tet.2012.02.047

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  9 in total

1.  Polynuclear azaarenes in wood preservative wastewater.

Authors:  J Adams; C S Giam
Journal:  Environ Sci Technol       Date:  1984-05-01       Impact factor: 9.028

2.  First total synthesis of phenylpyridine analogues of the antimitotic rhazinilam.

Authors:  E Pasquinet; P Rocca; S Richalot; F Guéritte; D Guénard; A Godard; F Marsais; G Quéguiner
Journal:  J Org Chem       Date:  2001-04-20       Impact factor: 4.354

3.  Direct synthesis of monofunctionalized indolizine derivatives bearing alkoxymethyl substituents at C-3 and their benzofused analogues.

Authors:  Joseph Kaloko; Anthony Hayford
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

4.  Theoretical study of aza-polycyclic aromatic hydrocarbons (aza-PAHs), modelling carbocations from oxidized metabolites and their covalent adducts with representative nucleophiles.

Authors:  Gabriela L Borosky; Kenneth K Laali
Journal:  Org Biomol Chem       Date:  2005-03-01       Impact factor: 3.876

5.  Synthesis of aza-fused polycyclic quinolines through copper-catalyzed cascade reactions.

Authors:  Qian Cai; Zhengqiu Li; Jiajia Wei; Liangbin Fu; Chengyong Ha; Duanqing Pei; Ke Ding
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

6.  Synthesis and mechanism of action studies of a series of norindenoisoquinoline topoisomerase I poisons reveal an inhibitor with a flipped orientation in the ternary DNA-enzyme-inhibitor complex as determined by X-ray crystallographic analysis.

Authors:  Alexandra Ioanoviciu; Smitha Antony; Yves Pommier; Bart L Staker; Lance Stewart; Mark Cushman
Journal:  J Med Chem       Date:  2005-07-28       Impact factor: 7.446

7.  Synthesis of phenol and quinone metabolites of benzo[a]pyrene, a carcinogenic component of tobacco smoke implicated in lung cancer.

Authors:  Daiwang Xu; Trevor M Penning; Ian A Blair; Ronald G Harvey
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

8.  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

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
  9 in total
  1 in total

1.  Superacid-promoted synthesis of quinoline derivatives.

Authors:  Hein Vuong; Michael R Stentzel; Douglas A Klumpp
Journal:  Tetrahedron Lett       Date:  2020-01-14       Impact factor: 2.415
  1 in total

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