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

doi:10.1055/s-2006-942462

PAPER

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;

Abstract

All articles of this category

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.

Key words

iodocyclization - isocyanate - isoindoline - 2-lithiostyrene - secondary benzamide

Full Text

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