Literature DB >> 25071296

Direct synthesis of arenecarboxamides through Friedel-Crafts acylation using ureas.

Wenjiang Ying1, Lalith S R Gamage1, Luke R Lovro1, James W Herndon1, Nathan W Jenkins1, James W Herndon1.   

Abstract

The reaction of urea derivatives that contain the phenothiazine unit with trifluoromethanesulfonic anhydride in the presence of electron-rich aromatic compounds leads to the formation of arenecarboxamides. The reaction has been successfully demonstrated for several inter- and intramolecular systems.

Entities:  

Year:  2014        PMID： 25071296      PMCID： PMC4111261          DOI： 10.1016/j.tetlet.2014.06.056

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


  12 in total

1.  Synthesis of fused phenothiazines. 2,3-dihydro-1H-pyrimido[5,6,1-Kl]phenothiazine-1,3-dione and 6H, 16H-[1,5]diazocino[3,2,1-kl:7,6,5-k'l']diphenothiazine-6,16-dione.

Authors:  J Weinstock; D E Gaitanopoulos; B M Sutton
Journal:  J Org Chem       Date:  1975-06-27       Impact factor: 4.354

2.  Friedel-Crafts-type reactions with ureas and thioureas.

Authors:  Erum K Raja; Sten O Nilsson Lill; Douglas A Klumpp
Journal:  Chem Commun (Camb)       Date:  2012-07-10       Impact factor: 6.222

3.  Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition.

Authors:  Sanghee Kim; Yun Mi Lee; Jaekwang Lee; Taeho Lee; Ye Fu; Yanling Song; Jihee Cho; Deukjoon Kim
Journal:  J Org Chem       Date:  2007-05-25       Impact factor: 4.354

4.  The urea renaissance.

Authors:  Nicole Volz; Jonathan Clayden
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-15       Impact factor: 15.336

5.  Asymmetric synthesis of (R)-antofine and (R)-cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde.

Authors:  Mingbo Cui; Hongjian Song; Anzheng Feng; Ziwen Wang; Qingmin Wang
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

6.  Asymmetric total syntheses of (-)-antofine and (-)-cryptopleurine using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol.

Authors:  Sanghee Kim; Taeho Lee; Eunjung Lee; Jaekwang Lee; Gao-jun Fan; Sang Kook Lee; Deukjoon Kim
Journal:  J Org Chem       Date:  2004-04-30       Impact factor: 4.354

7.  Synthesis and biological activities of some indolo[2,3-c]isoquinoline derivatives.

Authors:  G Winters; N Di Mola; M Berti; V Arioli
Journal:  Farmaco Sci       Date:  1979-06

8.  Anionic Indole N-carbamoyl N --> C translocation. A directed remote metalation route to 2-Aryl- and 2-heteroarylindoles. synthesis of benz[a]carbazoles and Indeno[1,2-b]indoles.

Authors:  Zhongdong Zhao; Ashley Jaworski; Isabel Piel; Victor Snieckus
Journal:  Org Lett       Date:  2008-06-11       Impact factor: 6.005

9.  Anionic N-fries rearrangement of N-carbamoyl diarylamines to anthranilamides. Methodology and application to acridone and pyranoacridone alkaloids.

Authors:  Stephen L MacNeil; Brian J Wilson; Victor Snieckus
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005

10.  A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas.

Authors:  Keith Smith; Gamal A El-Hiti; Amany S Hegazy; Benson Kariuki
Journal:  Beilstein J Org Chem       Date:  2011-09-06       Impact factor: 2.883
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  1 in total

1.  The [5+5] route to the phenanthrene skeleton.

Authors:  James W Herndon; Bishnu Dhakal
Journal:  ARKIVOC       Date:  2016-06-21       Impact factor: 1.140
  1 in total

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