Literature DB >> 22528272

Synthesis of benzopyrano[4,3-b](N-arylsulfonyl)indoles and benzopyrano[3,4-b](N-arylsulfonyl)indoles via intramolecular palladium-catalyzed aryl-aryl coupling reaction.

Ling-Ling Fan1, Zhi-Ping Che, Rui Zhang, Xiang Yu, Xiao-Yan Zhi, Hui Xu.   

Abstract

A series of benzopyrano[3,4-b](N-arylsulfonyl) indole derivatives and benzopyrano[4,3-b](N-arylsulfonyl) indole derivatives were synthesized from 2- or 3-methylindole via intermolecular S( N )2 reaction and subsequent intramolecular palladium-catalyzed aryl-aryl coupling reaction for the first time. It was suggested that, besides using the Fischer cyclization, benzopyrano[4,3-b]indoles and benzopyrano[3,4-b]indoles could also be prepared via intermolecular S( N )2 reaction and sequential intramolecular palladium-catalyzed coupling reaction.

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Year:  2012        PMID: 22528272     DOI: 10.1007/s11030-012-9370-5

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  9 in total

1.  Anti HIV-1 agents 5: synthesis and anti-HIV-1 activity of some N-arylsulfonyl-3-acetylindoles in vitro.

Authors:  Jun-Qiang Ran; Ning Huang; Hui Xu; Liu-Meng Yang; Min Lv; Yong-Tang Zheng
Journal:  Bioorg Med Chem Lett       Date:  2010-05-18       Impact factor: 2.823

2.  N-Arylsulfonylindole derivatives as serotonin 5-HT(6) receptor ligands.

Authors:  M G Russell; R J Baker; L Barden; M S Beer; L Bristow; H B Broughton; M Knowles; G McAllister; S Patel; J L Castro
Journal:  J Med Chem       Date:  2001-11-08       Impact factor: 7.446

3.  Optimization of small molecule agonists of the thrombopoietin (Tpo) receptor derived from a benzo[a]carbazole hit scaffold.

Authors:  Thomas H Marsilje; Phil B Alper; Wenshuo Lu; Daniel Mutnick; Pierre-Yves Michellys; Yun He; Donald S Karanewsky; Donald Chow; Andrea Gerken; Jianmin Lao; Min-Ju Kim; H Martin Seidel; Shin-Shay Tian
Journal:  Bioorg Med Chem Lett       Date:  2008-08-26       Impact factor: 2.823

4.  1,3,6-trisubstituted indoles as peptidoleukotriene antagonists: benefits of a second, polar, pyrrole substituent.

Authors:  F J Brown; L A Cronk; D Aharony; D W Snyder
Journal:  J Med Chem       Date:  1992-06-26       Impact factor: 7.446

5.  Carcinogenic nitrogen compounds. LXXX. (1)Benzopyrano-(4,3-b)indoles and 6H-(1)benzopyrano(4,3-b)quinolines.

Authors:  N P Buu-Hoï; A Croisy; P Jacquignon; D P Hien; A Martani; A Ricci
Journal:  J Chem Soc Perkin 1       Date:  1972

6.  Anti human immunodeficiency virus-1 (HIV-1) agents 3. synthesis and in vitro anti-HIV-1 activity of some N-arylsulfonylindoles.

Authors:  Ling-Ling Fan; Wu-Qing Liu; Hui Xu; Liu-Meng Yang; Min Lv; Yong-Tang Zheng
Journal:  Chem Pharm Bull (Tokyo)       Date:  2009-08       Impact factor: 1.645

7.  2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones.

Authors:  M Artico; R Silvestri; S Massa; A G Loi; S Corrias; G Piras; P La Colla
Journal:  J Med Chem       Date:  1996-01-19       Impact factor: 7.446

8.  Carcinogenic nitrogen compounds. LII. [1]benzothiopyrano-[4,3-b]indoles, [1]benzopyrano[4,3-b]indoles, and related pseudo-azulenes.

Authors:  N P Buu-Hoï; A Martani; A Croisy; P Jacquignon; F Périn
Journal:  J Chem Soc Perkin 1       Date:  1966

9.  One-pot N-arylation of indoles directly from N-arylsulfonylindoles via consecutive deprotection and S(N)Ar Reactions with activated Aryl halides.

Authors:  Hui Xu; Ling-Ling Fan
Journal:  Chem Pharm Bull (Tokyo)       Date:  2009-03       Impact factor: 1.645

  9 in total

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