Download PDF
Synlett 2002(2): 0343-0345
DOI: 10.1055/s-2002-19765
LETTER
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Parallel Synthesis of a 2-Aryl-1H-Isoindole-1,3-Dione Library

Bernardo M. Barchín, Ana M. Cuadro, Julio Alvarez-Builla*
Departamento de Química Orgánica, Universidad de Alcalá, Ctra. Madrid-Barcelona Km 33,600, C.P. 28871, Alcalá de Henares, Madrid, Spain
Fax: +34(91)8854686; e-Mail: julio.alvarez@uah.es;
Further Information

Publication History

Received 25 October 2001
Publication Date:
02 February 2007 (online)

    Permissions and Reprints All articles of this category

Abstract

An efficient parallel synthesis of a representative 28-member library of phthalimides is described. Parallel chromatography afforded the library members in suitable purity and with high yields.

Key words

library - microwave - phthalimide - 2-aryl-1H-isoindole-1,3-dione - TNF-α

    References

  • For some recent biological applications, see:
  • 1a Shimazawa R. Miyachi H. Takayama H. Kuroda K. Kato F. Kato M. Hashimoto Y. Biol. Pharm. Bull.  1999,  22:  224 
    CrossrefGoogle Scholar
  • 1b Da Settimo A. Primofiore G. Da Settimo F. Simorini F. La Motta C. Martinelli A. Boldrine E. Eur. J. Med. Chem.  1996,  31:  49 
    CrossrefGoogle Scholar
  • 1c Shibata Y. Sasaki K. Hashimoto Y. Iwasaki S. Chem. Pharm. Bull.  1996,  44:  156 
    CrossrefGoogle Scholar
  • 1d Langmuir ME. Yang J.-R. Moussa AM. Laura R. Lecompte KA. Tetrahedron Lett.  1995,  36:  3989 
    CrossrefGoogle Scholar
  • 1e Mayer A. Neuenhofer S. Angew. Chem. Int. Ed. Engl.  1994,  33:  1044 
    CrossrefGoogle Scholar
  • 1f Rusiecki VK. Warner SA. Bioorg. Med. Chem. Lett.  1993,  3:  707 
    CrossrefGoogle Scholar
  • 2a Reddy PY. Kondo S. Toru T. Ueno Y. J. Org. Chem.  1997,  62:  2652 ; and references cited therein
    CrossrefGoogle Scholar
  • 2b Ohkubo M. Nishimura T. Jona H. Honma T. Morishima H. Tetrahedron  1996,  52:  8099 
    CrossrefGoogle Scholar
  • 3 Iijima T. Suzuki N. Fukuda W. Tomoi M. J. Eur. Polym.  1995,  31:  775 
    CrossrefGoogle Scholar
  • 4a Walker MA. J. Org. Chem.  1995,  60:  5352 
    CrossrefGoogle Scholar
  • 4b Walker MA. Tetrahedron Lett.  1994,  35:  665 
    CrossrefGoogle Scholar
  • 5 Bogdal D. Pielichowsky J. Boron A. Synlett  1996,  873 
    Article in Thieme ConnectGoogle Scholar
  • For recent papers see:
  • 6a Vidal T. Petit A. Loupy A. Gedye RN. Tetrahedron  2000,  56:  5473 
    CrossrefGoogle Scholar
  • 6b Seijas JA. Vazquez-Tato P. Martinez MM. Nuñez-Corredoira G. J. Chem. Res. (S)  1999,  420 
    CrossrefGoogle Scholar
  • 6c Varma RS. Dahiya R. Kumar S. Tetrahedron Lett.  1997,  38:  2039 
    CrossrefGoogle Scholar
  • 7a Chandrasekhar S. Padmaja NB. Raza A. Synlett  1999,  1597 
    CrossrefGoogle Scholar
  • 7b Chandrasekhar S. Takhi M. Uma G. Tetrahedron Lett.  1997,  38:  8089 
    CrossrefGoogle Scholar
  • 8 Borah NH. Boruah RC. Sandhus JS. J. Chem. Res.(S)  1998,  272 
    CrossrefGoogle Scholar
  • Parallel synthesis in microwave ovens has been described to prepare thioamide and pyridine libraries:
  • 9a Olsson R. Hansen HC. Andersson C.-M. Tetrahedron Lett.  2000,  41:  7947 
    CrossrefGoogle Scholar
  • 9b Cotterill IC. Usyatinsky AY. Arnold JM. Clark DS. Dordick JS. Michels PC. Khmelnitsky YL. Tetrahedron Lett.  1998,  39:  1117 
    CrossrefGoogle Scholar
  • 10 Microwave irradiation was carried out with a Sanyo microwave oven (EM-S100, 800, with a maximum power output of 800 W) calibrated by a standard procedure: Watkins KW. J. Chem. Ed.  1983,  60:  1043 
    Google Scholar
  • 14 Shibata Y. Sasaki K. Hashimoto Y. Iwasaki S. Chem. Pharm. Bull.  1996,  44:  156 
    CrossrefGoogle Scholar
  • 15 Kamal A. Laxman E. Laxman N. Rao V. Tetrahedron Lett.  1998,  39:  8733 
    CrossrefGoogle Scholar
  • 16 Pagani G. Baruffini A. Borgna P. Caccialanza G. Farmaco, Ed. Sci.  1968,  23:  448 ; Chem. Abstr. 1969, 69, 43588
    Google Scholar
  • 17 Miyachi H. Azuma A. Ogasawara A. Uchimura E. Watanabe N. Kobayashi Y. Kato F. Kato M. Hashimoto Y. J. Med. Chem.  1997,  40:  2858 
    CrossrefGoogle Scholar
  • 18 Fifolt M. J., Sojka S. A., Wolfe R. A., Hojnicki D. S., Bieron J. F., Dinan F. J.; J. Org. Chem.; 1989, 54: 3019
  • 19 Abdel-Rahman AE. Khalil ZH. Bull. Chem. Soc. Jpn.  1978,  51:  2148 
    Google Scholar
  • 20 Krische MJ. Lehn JM. Kyritsakas N. Fisher J. Helv. Chim. Acta  1998,  81:  1909 
    CrossrefGoogle Scholar
  • 21 Perry RJ. Turner R. J. Org. Chem.  1991,  56:  6573 
    CrossrefGoogle Scholar
  • 23 Hasimoto Y. inventors; PCT Int. Appl.  WO9807421.  ; Chem. Abstr. 1998, 128, 204894.
11

Acquired from International Sorbent Technology Ltd., U.K.

12

Savant Automatic Environmental SpeedVac (AES 2000) was used.

13

Microsoft® Excel 97 was used.

22

Hokko Chemical Industry Co. Ltd., Jpn. Kokai Tokkyo Koh, 1980, Jp55136210A2; Chem. Abstr. 1980, 94, 78435.