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Synthesis 2011(1): 147-153  
DOI: 10.1055/s-0030-1258313
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise and Flexible Diastereoselective Approach to Heteroring-Fused Isoindolinones

Gang Ahna,b, Magali Loriona,b, Vangelis Agouridasa,b, Axel Couture*a,c, Eric Deniaua,b, Pierre Grandclaudona,b
a Univ Lille Nord de France, 59000 Lille, France
Fax: +33(0)320436309; e-Mail: axel.couture@univ-lille1.fr;
b USTL, Laboratoire de Chimie Organique Physique, EA CMF 4478, Bâtiment C3(2), 59655 Villeneuve d’Ascq, France
c CNRS, UMR 8181 ‘UCCS’, 59655 Villeneuve d’Ascq, France
Further Information

Publication History

Received 7 September 2010
Publication Date:
25 October 2010 (online)

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Abstract

A variety of poly and diversely substituted isoindoli­nones fused with six-membered heterocyclic moieties has been readily assembled through a sequence involving metalation of N-chloroalkylated models, subsequent interception with appropriate electrophiles and ultimate intramolecular annulation reaction.

Key words

carbanions - fused-ring systems - lactams - metalation - cyclization

    References

  • 1a Hamprecht D. Micheli F. Tedesco G. Checchia A. Donati D. Petrone M. Terreni S. Wood M. Bioorg. Med. Chem. Lett.  2007,  17:  428 
    Google Scholar
  • 1b Jagtap PG. Southan GJ. Baloglu E. Ram S. Mabley JG. Marton A. Salzman A. Szabó C. Bioorg. Med. Chem. Lett.  2004,  14:  81 
    Google Scholar
  • 1c Kundu NG. Khan MW. Mukhopadhyay R. J. Indian Chem. Soc.  2001,  78:  671 
    Google Scholar
  • 1d Muller GW. Chen R. Huang S.-Y. Corral LG. Wong LM. Patterson RT. Chen Y. Kaplan G. Stirling DI. Bioorg. Med. Chem. Lett.  1999,  9:  1625 
    Google Scholar
  • 1e Norman MH. Minick DJ. Rigdon GC. J. Med. Chem.  1996,  39:  149 
    Google Scholar
  • 1f Schäfer W. Friebe W.-G. Leinert H. Mertens A. Poll T. von der Saal W. Zilch H. Nuber B. Ziegler ML.
    J. Med. Chem.  1993,  36:  726 
    Google Scholar
  • 1g Kato Y. Takemoto M. Achiwa K. Chem. Pharm. Bull.  1993,  41:  2003 
    Google Scholar
  • 1h Aboudi AF. Al-Eisawi DM. Sabri SS. Abu Zarga MH. J. Nat. Prod.  1986,  49:  370 
    Google Scholar
  • 1i Blaskó G. Gula DJ. Shamma M. J. Nat. Prod.  1982,  45:  105 
    Google Scholar
  • 1j Hussain SF. Minard RD. Freyer AJ. Shamma M. J. Nat. Prod.  1981,  44:  169 
    Google Scholar
  • 2a Shinji C. Maeda S. Imai K. Yoshida M. Hashimoto Y. Miyachi H. Bioorg. Med. Chem. Lett.  2006,  14:  7625 
    Google Scholar
  • 2b Shinozuka T. Yamamoto Y. Hasegawa T. Saito K. Naito S. Tetrahedron Lett.  2008,  49:  1619 
    Google Scholar
  • 3a Zhuang Z.-P. Kung M.-P. Mu M. Kung HF. J. Med. Chem.  1998,  41:  157 
    Google Scholar
  • 3b Reiffen M. Eberlein W. Mueller P. Psiorz M. Noll K. Heider J. Lillie C. Kobinger W. Luger P. J. Med. Chem.  1990,  33:  1496 
    Google Scholar
  • 4 Csende F. Stajer G. Curr. Org. Chem.  2005,  9:  1261 
    CrossrefGoogle Scholar
  • 5 Mertens A. Zilch H. König B. Schäfer W. Poll T. Kampe W. Seidel H. Leser U. Leinert H. J. Med. Chem.  1993,  36:  2526 
    CrossrefPubMedGoogle Scholar
  • 6 Lübbers T. Angehrn P. Gmünder H. Herzig S. Bioorg. Med. Chem. Lett.  2007,  24:  4708 
    Google Scholar
  • 7 Wacker DA. Varnes JG. Malmstrom SE. Cao X. Hung C.-P. Ung T. Wu G. Zhang G. Zuvich E. Thomas MA. Keim WJ. Cullen MJ. Rohrbach KW. Qu Q. Narayanan R. Rossi K. Janovitz E. Lehman-McKeeman L. Malley MF. Devenny J. Pelleymounter MA. Miller KJ. Robl JA. J. Med. Chem.  2007,  50:  1365 
    CrossrefGoogle Scholar
  • 8 Martini E. Norcini M. Ghelardini C. Manetti D. Dei S. Guandalini L. Melchiorre M. Pagella S. Scapecchi S. Teodori E. Romanelli MN. Bioorg. Med. Chem.  2008,  16:  10034 
    CrossrefGoogle Scholar
  • 9a Ghosh U. Bhattacharyya R. Keche A. Tetrahedron  2010,  66:  2148 ; and references cited therein
    Google Scholar
  • 9b Kim SH. Kim SH. Kim KH. Kim JN. Tetrahedron Lett.  2010,  51:  860 ; and references cited therein
    Google Scholar
  • 10a Chiurato M. Boulahjar R. Routier S. Troin Y. Guillaumet G. Tetrahedron  2010,  66:  4647 
    Google Scholar
  • 10b Medimagh R. Marque S. Prim D. Marrot J. Chatti S. Org. Lett.  2009,  11:  1817 
    Google Scholar
  • 10c Murai M. Miki K. Ohe K. J. Org. Chem.  2008,  73:  9174 
    Google Scholar
  • 10d Salcedo A. Neuville L. Zhu J. J. Org. Chem.  2008,  73:  3600 
    Google Scholar
  • 10e Bertus P. Menant C. Tanguy C. Szymoniak J. Org. Lett.  2008,  10:  777 
    Google Scholar
  • 10f Sun C. Xu B. J. Org. Chem.  2008,  73:  7361 
    Google Scholar
  • 10g He Z. Yudin AK. Org. Lett.  2006,  8:  5829 
    Google Scholar
  • 10h Kobayashi K. Hase M. Hashimoto K. Fujita S. Tanmatsu M. Morikawa O. Konishi H. Synthesis  2006,  2493 
    Google Scholar
  • 10i Majumdar KC. Das TK. Jana M. Synth. Commun.  2005,  35:  1961 
    Google Scholar
  • 10j Stajer G. Csende F. Curr. Org. Chem.  2005,  9:  1277 
    Google Scholar
  • 10k Osante I. Lete E. Sotomayor N. Tetrahedron Lett.  2004,  45:  1253 
    Google Scholar
  • 10l Bahajaj AA. Vernon JM. Wilson GD. Tetrahedron  2004,  60:  1247 
    Google Scholar
  • 10m Bertus P. Szymoniak J. J. Org. Chem.  2003,  68:  7133 
    Google Scholar
  • 10n Deville JP. Behar V. Org. Lett.  2002,  4:  1403 
    Google Scholar
  • 10o Enders D. Braig V. Raabe G. Can. J. Chem.  2001,  79:  1528 
    Google Scholar
  • 10p Campbell JB. Dedinas RF. Trumbower-Walsh SA. J. Org. Chem.  1996,  61:  6205 
    Google Scholar
  • 10q Araki S. Shimizu T. Johar PS. Jin SJ. Butsugan Y. J. Org. Chem.  1991,  56:  2538 
    Google Scholar
  • 11a Lorion M. Couture A. Deniau E. Grandclaudon P. Synthesis  2008,  2141 
    Google Scholar
  • 11b Lorion M. Couture A. Deniau E. Grandclaudon P. J. Org. Chem.  2006,  71:  3303 
    Google Scholar
  • 12a Couture A. Deniau E. Ionescu D. Grandclaudon P. Tetrahedron Lett.  1998,  39:  2319 
    Google Scholar
  • 12b Guo Z. Schultz AG. J. Org. Chem.  2001,  66:  2154 
    Google Scholar
  • 14 Lorion M. Couture A. Deniau E. Grandclaudon P. Synthesis  2009,  1897 
    Article in Thieme ConnectGoogle Scholar
  • 15 Tongshou J. Guoliang F. Mina Y. Tongshuang L. Synth. Commun.  2004,  34:  1277 
    CrossrefGoogle Scholar
13

Selected X-ray crystallographic data for 9j: Empirical formula: C19H19NO4; Mr = 325.35 g˙mol-¹; F(000) = 688; white crystal; D = 1.353 g˙cm-³; µ(Mo Kα) = 0.095; monoclinic; P21/n; a = 5.56820 (10) Å, b = 8.60050 (10) Å, c = 33.3710 (6) Å; α = 90.00, β = 91.8710 (10), γ = 90.00; V = 1597.26 (4) ų; Z = 4; T = 100 K. Further details of the X-ray structure data are available on request from the Cambridge Crystallographic Data Centre (CCDC 791641)