Literature DB >> 19572201

A suitable preparation of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and their ring homologs with a reusable Preyssler heteropolyacid as catalyst.

Gustavo P Romanelli1, Diego M Ruiz, Juan C Autino, Héctor E Giaccio.   

Abstract

The preparation of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines, N-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines and N-sulfonyl-1,2,3,4,5,6-hexahydrobenzazocine was catalyzed by a Preyssler heteropolyacid, H(14)[NaP(5)W(30)O(110)], (PA), supported on silica (PASiO(2)40) with excellent yields by means of the Pictet-Spengler reaction of N-aralkylsulfonamides with s-trioxane. The reactions proceed with 0.5 mol% of silica-supported catalyst in toluene at 70°C. The catalyst can be recycled without appreciable loss of the catalytic activity.

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Year:  2009        PMID: 19572201     DOI: 10.1007/s11030-009-9173-5

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


  13 in total

1.  Heterogeneous Catalysis.

Authors:  Noritaka Mizuno; Makoto Misono
Journal:  Chem Rev       Date:  1998-02-05       Impact factor: 60.622

Review 2.  Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics.

Authors:  Jack D Scott; Robert M Williams
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

3.  Water-tolerant solid acid catalysts.

Authors:  Toshio Okuhara
Journal:  Chem Rev       Date:  2002-10       Impact factor: 60.622

4.  Protection (and deprotection) of functional groups in organic synthesis by heterogeneous catalysis.

Authors:  Giovanni Sartori; Roberto Ballini; Franca Bigi; Giovanna Bosica; Raimondo Maggi; Paolo Righi
Journal:  Chem Rev       Date:  2004-01       Impact factor: 60.622

5.  Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis.

Authors:  Avelino Corma; Hermenegildo García
Journal:  Chem Rev       Date:  2003-11       Impact factor: 60.622

6.  Complete 1H and 13C NMR spectral assignment of N-aralkylsulfonamides, N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and N-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines. Conformational analysis of N-[((3',4'-dichlorophenyl)methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin.

Authors:  Jorge L Jios; Gustavo P Romanelli; Juan Carlos Autino; Héctor E Giaccio; Helmut Duddeck; Michael Wiebcke
Journal:  Magn Reson Chem       Date:  2005-12       Impact factor: 2.447

7.  Aqua mediated synthesis of substituted 2-amino-4H-chromenes catalyzed by green and reusable Preyssler heteropolyacid.

Authors:  Majid M Heravi; Khadijeh Bakhtiari; Vahideh Zadsirjan; Fatemeh F Bamoharram; Omid M Heravi
Journal:  Bioorg Med Chem Lett       Date:  2007-05-16       Impact factor: 2.823

8.  A convenient synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines via Pictet-Spengler reaction using titanium(IV) isopropoxide and acetic-formic anhydride.

Authors:  Yoshie Horiguchi; Hirokazu Kodama; Masayoshi Nakamura; Tsuyoshi Yoshimura; Kaori Hanezi; Hiroko Hamada; Toshiaki Saitoh; Takehiro Sano
Journal:  Chem Pharm Bull (Tokyo)       Date:  2002-02       Impact factor: 1.645

9.  Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents.

Authors:  K Iwasa; M Moriyasu; Y Tachibana; H S Kim; Y Wataya; W Wiegrebe; K F Bastow; L M Cosentino; M Kozuka; K H Lee
Journal:  Bioorg Med Chem       Date:  2001-11       Impact factor: 3.641

10.  1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro.

Authors:  Pi Cheng; Ning Huang; Zhi-Yong Jiang; Quan Zhang; Yong-Tang Zheng; Ji-Jun Chen; Xue-Mei Zhang; Yun-Bao Ma
Journal:  Bioorg Med Chem Lett       Date:  2008-02-19       Impact factor: 2.823

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  1 in total

1.  An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using recyclable alumina-supported heteropolyoxometalates.

Authors:  Diego M Ruiz; Juan C Autino; Nancy Quaranta; Patricia G Vázquez; Gustavo P Romanelli
Journal:  ScientificWorldJournal       Date:  2012-03-12
  1 in total

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