Synthesis 2006(15): 2493-2496  
DOI: 10.1055/s-2006-942462
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3,3-Disubstituted Isoindolin-1-ones via Iodoamination of α-Substituted Secondary 2-Vinylbenzamides

Kazuhiro Kobayashi*, Masanori Hase, Kenichi Hashimoto, Seiki Fujita, Miyuki Tanmatsu, Osamu Morikawa, Hisatoshi Konishi
Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
Further Information

Publication History

Received 3 March 2006
Publication Date:
04 July 2006 (eFirst)

Abstract

A new and simple method for the preparation of 3,3-di­substituted isoindolin-1-ones from α-substituted 2-bromostyrenes is described. Construction of the isoindolin-1-one skeleton was accomplished by treating α-substituted secondary 2-vinylbenzamides, easily obtainable from the reaction of α-substituted 2-lithiostyrenes with isocyanates, with iodine to afford 3-substituted 3-iodomethylisoindolin-1-ones.

    References

  • For a review:
  • 1a Stajer G. Csende F. Curr. Org. Chem.  2005,  9:  1277 
  • For recent reports:
  • 1b Couture A. Deniau E. Ionescu D. Grandclaudon P. Tetrahedron Lett.  1998,  39:  2319 
  • 1c Allin SM. Northfield CJ. Page MI. Slawin AMZ. J. Chem. Soc., Perkin Trans. 1  2000,  1715 
  • 1d Yoda H. Matsuda K. Nomura H. Takabe K. Tetrahedron Lett.  2000,  41:  1775 
  • 1e Deniau E. Enders D. Tetrahedron Lett.  2000,  41:  2347 
  • 1f Kundu NG. Khan MW. Tetrahedron  2000,  56:  4777 
  • 1g Luo F.-T. Chen C.-H. Heterocycles  2001,  55:  1663 
  • 1h Guo Z. Schultz AG. J. Org. Chem.  2001,  66:  2154 
  • 1i Deniau E. Enders D. Tetrahedron  2001,  57:  2581 
  • 1j Knepper K. Ziegler RE. Bräse S. Tetrahedron  2004,  60:  8591 
  • New methods for the preparation of 3-unsubstituted isoindolin-1-ones have also been reported recently:
  • 1k Delacroix T. Bérillon L. Cahiez G. Knochel P. J. Org. Chem.  2000,  65:  8108 
  • 1l Takahashi I. Kawakami T. Kimino M. Hirano E. Kamimura S. Tamura T. Kitajima H. Hatanaka M. Uchida H. Nomura A. Tanaka M. Heterocycles  2001,  54:  635 
  • 2a Breytenbach JC. van Dyk S. van den Heever I. Allin SM. Hodkinson CC. Northfield CJ. Page MI. Bioorg. Med. Chem. Lett.  2000,  10:  1629 
  • 2b Jagtap PG. Southan GJ. Baloglu E. Ram S. Mabley JG. Marton A. Salzman A. Szabo C. Bioorg. Med. Chem. Lett.  2004,  14:  81 
  • 2c Curtin ML. Frey RR. Robin Heyman H. Sarris KA. Steinman DH. Holmes JH. Bousquet PF. Cunha GA. Moskey MD. Ahmed AA. Pease LJ. Glaser KB. Stewart KD. Davidsen SK. Michaelides MR. Bioorg. Med. Chem. Lett.  2004,  14:  4505 
  • 2d Hardcastle IR. Ahmed SU. Atkins H. Calvert AH. Curtin NJ. Farnie G. Golding BT. Griffin RJ. Guyenne S. Hutton C. Källblad P. Kemp SJ. Kitching MS. Newell DR. Norbedo S. Northen JS. Reid RJ. Saravanan K. Willems HMG. Lunec J. Bioorg. Med. Chem. Lett.  2005,  15:  1515 
  • 3a Berti G. Gazz. Chim. Ital.  1960,  90:  559 
  • 3b Recently, Comins et al. demonstrated an asymmetric synthesis of 3,3-disubstituted isoindolin-1-one derivatives by alkylation of (-)-trans-2-(α-cumyl)cyclohexyl 3-methyl-1-oxoisoindolin-2-carboxylate: Comins DL. Hiebel A.-C. Tetrahedron Lett.  2005,  46:  5639 
  • 4 Kobayashi K. Miyamoto K. Morikawa O. Konishi H. Bull. Chem. Soc. Jpn.  2005,  78:  886 
  • 5 After completion of the present work, we became aware of a publication by Larock and Yao, who reported a synthesis of 3-(2-iodoalkynylidene)isoindol-1-ones by iodocyclization of secondary 2-(1-alkynyl)benzamides: Yao T. Larock RC. J. Org. Chem.  2005,  70:  1432 
  • 6 Jason ME. Tetrahedron Lett.  1982,  23:  1635 
  • 7 Fleming I. Woolias M. J. Chem. Soc., Perkin Trans. 1  1979,  829 
  • 8 Morrow GW. Marks TM. Sear DL. Tetrahedron  1995,  51:  10115