A Convenient Synthesis of 4-Alkoxylated Isoindolin-1-ones

Anne Moreau; Axel Couture; Eric Deniau; Pierre Grandclaudon

doi:10.1055/s-2004-829114

PAPER

A Convenient Synthesis of 4-Alkoxylated Isoindolin-1-ones

Anne Moreau, Axel Couture*, Eric Deniau, Pierre Grandclaudon
Laboratoire de Chimie Organique Physique, UMR 8009 ‘Laboratoire de Chimie Organique et Macromoléculaire’, Université des Sciences et Technologies de Lille, Bâtiment C3(2), 59655 Villeneuve d"Ascq Cédex, France
Fax: +33(3)20336119; e-Mail: axel.couture@univ-lille1.fr;

Abstract

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Abstract

A short synthesis of 4-alkoxylated isoindolin-1-ones based upon the S_NAr reaction applied to phosphorylated 2-methoxybenzamides followed by alkaline cleavage of the phosphoryl auxiliary is reported.

Key words

metalations - carbanions - nucleophilic aromatic substitutions - ring closure - cleavage

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References

1 Shamma M. Moniot J.-L. J. Chem. Soc., Chem. Commun. 1975, 89

2 Valencia E. Freyer AJ. Shamma M. Fajardo V. Tetrahedron Lett. 1984, 25: 599

3 Fuchs JR. Funk RL. Org. Lett. 2001, 3: 3923

4a Fajardo V. Elango V. Cassels BK. Shamma M. Tetrahedron Lett. 1982, 23: 39

4b Fang FG. Danishefsky SJ. Tetrahedron Lett. 1989, 30: 2747

5 Lawrence NJ. Liddle J. Bushell SM. Jackson DA. J. Org. Chem. 2002, 67: 457

6a Kondo T. Yoshida K. Yamamoto M. Tanayama S. Arzneim. Forsch. 1996, 46: 11

6b Linden M. Hadler D. Hofmann S. Human Psychopharm. 1997, 12: 445

7 Yamabe H, Okuyama M, Nakao A, Ooizumi M, and Saito K. inventors; PCT Int. Appl. WO 2001064670. ; Chem. Abstr. 2001, 135, 226879

8 Biller SA, Dickson JK, Lawrence RM, Magnin DR, Poss MA, Sulsky RB, and Tino JA. inventors; US Patent US 5739135. ; Chem. Abstr. 1998, 128, 282780

9 Bengtsson KS, Thorberg SO, and Oegren SO. inventors; Eur. Pat. App. EP 26749. ; Chem. Abstr. 1981, 95, 62013

10 Inaba T, Kaya T, and Iwamura H. inventors; PCT Int. Appl. WO 9729079. ; Chem. Abstr. 1997, 127, 190528

11 Suemitsu R. Ohnishi K. Morikawa Y. Nagamoto S. Phytochemistry 1995, 38: 495

12 Horiuchi M. Maoka T. Iwase N. Ohnishi K. J. Nat. Prod. 2002, 65: 1204

13 Tojo E. Dominguez D. Castedo L. Phytochemistry 1991, 30: 1005

14a Pendergast W. Dickerson SH. Dev IK. Ferone R. Duch DS. Smith GK. J. Med. Chem. 1994, 37: 838

14b Taylor EC. Jennings LD. Mao Z. Hu B. Jun J.-G. Zhou P. J. Org. Chem. 1997, 62: 5392

14c Wang H. Ganesan A. Tetrahedron Lett. 1998, 39: 9097

15 Anderson PS. Christy ME. Colton CD. Shepard KL. J. Org. Chem. 1978, 43: 3719

16 Kigazawa K, Hiiragi M, Ishimaru H, Haga S, and Shirayama K. inventors; Japanese Patent JP 54092954. ; Chem. Abstr. 1980, 92, 76287

17 Takahashi I. Hirano E. Kawkani T. Kitajima H. Heterocycles 1996, 43: 2343

18a Becke F, and Jagla E. inventors; British Patent GB 1049007. ; Chem. Abstr. 1967, 66, 37763

18b Norman MH. Kelley JL. Hollingsworth EB. J. Med. Chem. 1993, 36: 3417

19a Mori M. Chiba K. Ban Y. J. Org. Chem. 1978, 43: 1684

19b Anderson JC. Flaherty A. Schwarbrick ME. J. Org. Chem. 2000, 65: 9152

20 Anzini M. Capelli A. Vomero S. Heterocycles 1994, 38: 103

21 Grigg R. Zhang L. Collard S. Keep A. Tetrahedron Lett. 2003, 44: 6979

22 Shah JH. Swartz GM. Papathanassiu AE. Treston AM. Fogler WE. Madsen JW. Green SJ. J. Med. Chem. 1999, 42: 3014

23 Couture A. Deniau E. Grandclaudon P. Lebrun S. Tetrahedron: Asymmetry 2003, 14: 1309

24 Hoarau C. Couture A. Deniau E. Grandclaudon P. J. Org. Chem. 2002, 67: 5846

25a Couture A. Deniau E. Grandclaudon P. Hoaurau C. J. Org. Chem. 1998, 63: 3128

25b Hoarau C. Couture A. Cornet H. Deniau E. Grandclaudon P. J. Org. Chem. 2001, 66: 8064

26 For a recent paper, see: Hattori T. Takeda A. Suzuki K. Koike N. Koshiishi E. Miyano S. J. Chem. Soc., Perkin Trans. 1 1998, 3661

27 Clayden J. Menet CJ. Tetrahedron Lett. 2003, 44: 3059

28 Gant TG. Meyers AI. Tetrahedron 1994, 50: 2297

29a Allen DW. Hutley BG. Mellor MTJ. J. Chem. Soc., Perkin Trans. 2 1977, 1705

29b Hoarau C. Couture A. Deniau E. Grandclaudon P. Synthesis 2000, 655

29c Eymery F. Iorga B. Savignac P. Tetrahedron 1999, 55: 13109

30 Datta SC. Murti VVS. Seshadri TR. Indian J. Chem. 1969, 7: 110

31 Loyd HA. Warren KS. Fales HM. J. Am. Chem. Soc. 1966, 88: 5544

32 Giles RGF. Green IR. Gruchlik Y. Oosthuizen FJ. Austr. J. Chem. 2000, 53: 341

33 Loriot M. Robin J.-P. Brown E. Tetrahedron 1984, 40: 2529

34 Garcia A. Castedo L. Dominguez D. Tetrahedron 1995, 51: 8585

35 Couture A. Deniau E. Grandclaudon P. Lebrun S. Tetrahedron Lett. 1996, 37: 7749

36 Barr N. Bartley JP. Clark PW. Dunstan P. Dyke SF. J. Organomet. Chem. 1986, 302: 117