A new and versatile synthetic route to 2-dimethylamino-3-alkyl and arylmethylene-2,3-dihydro-1H-isoindol-1-ones

Tetrahedron Letters

Volumn 43, Issue 45, 2002, Pages 8055-8058

  Deniau, Eric ^a   Enders, Dieter ^b  

^a UNIV LILLE   (France)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Benzotriazole; Carbanions; Enamides; Hydrazides; Isoindolinones

Indexed keywords

ACID; KETONE DERIVATIVE; METHYLENE 2,3 DIHYDRO 1H ISOINDOL 1 ONE; UNCLASSIFIED DRUG;

ACIDITY; ALKYLATION; ARTICLE; DRUG SYNTHESIS; ELIMINATION REACTION; MODEL; PROTON TRANSPORT;

EID: 0037020636     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01972-X     Document Type: Article

References (43)

1. Uozumi Y., Kawasaki N., Mori E., Mori M., Shibasaki M. J. Am. Chem. Soc. 111:1989;3725-3727.
2. Liebeskind L.S., Johnson S.A., McCallum J.S. Tetrahedron Lett. 31:1990;4397-4400.
3. Couture A., Deniau E., Grandclaudon P. Tetrahedron. 53:1997;10313-10330.
4. Daich A., Marchalin S., Pigeon P., Decroix B. Tetrahedron Lett. 39:1998;9187-9190.
5. Kundu N.G., Khan M.W. Tetrahedron. 56:2000;4777-4792.
6. Kato Y., Ebiike H., Achiwa K., Ashizawa N., Kurihara T., Kobayashi F. Chem. Pharm. Bull. 38:1990;2060-2062.
7. Kim J.N., Ryu E.K. Synth. Commun. 26:1996;67-74.
8. Ghorab M.M., Nassar O.M., Hassan A.Y. Phosphorus Sulfur Silicon Relat. Elem. 134/135:1998;57-76.
9. Kato Y., Takemoto M., Achiwa K. Chem. Pharm. Bull. 47:1999;529-535.
10. Cid H.M.B., Traenkle C., Baumann K., Pick R., Mies-Klomfass E., Kostenis E., Mohr K., Holzgrabe U. J. Med. Chem. 43:2000;2155-2164.
11. Valencia E., Weiss I., Firdous S., Freyer A.J., Shamma M., Urzua A., Fayardo V. Tetrahedron. 40:1984;3957-3962.
12. Ruchirawat S., Lertwanawatana W., Thianpatanagal S., Cashaw J.L., Davies V.E. Tetrahedron Lett. 25:1984;3485-3488.
13. Priestap H.A. Phytochemistry. 24:1985;849-852.
14. Fang F.G., Fiegelson G.B., Danishefsky S.J. Tetrahedron Lett. 30:1989;2743-2746.
15. Castedo L., Guitian E., Saa J.M., Suau R. Heterocycles. 19:1982;279-280.
16. Estevez J.C., Villaverde M.C., Estevez R.J., Castedo L. Tetrahedron. 51:1995;4075-4082.
17. Couture A., Deniau E., Grandclaudon P., Lebrun S. Synlett. 1997;1475-1477.
18. Couture A., Deniau E., Grandclaudon P., Hoarau C. J. Org. Chem. 63:1998;3128-3132.
19. Hoarau C., Couture A., Cornet H., Deniau E., Grandclaudon P. J. Org. Chem. 66:2001;8064-8069.
20. Ishibashi H., Kawanami H., Ikeda M. J. Chem. Soc., Perkin Trans. 1. 1997;817-821.
21. Couture A., Deniau E., Grandclaudon P., Hoarau C. Tetrahedron. 56:2000;1491-1499.
22. El-Maghraby A.A., Bedair A.H., Aly F.M., Emam H.A. Indian J. Chem. Sect. B. 26:1987;979-982.
23. Scartoni V., Morelli I., Marsili A., Catalano S. J. Chem. Soc., Perkin Trans. 1. 1977;2332-2336.
24. Vasilevskii S.F., Pozdnyakov A.V., Shvartsberg M.S. Izv. Akad. Nauk. SSSR, Ser. Khim. 1985;1367-1370.
25. Rowe F.M., Adams D.A.W., Peters A.T., Gillam A.E. J. Chem. Soc. 1937;90-109.
26. Thompson J.M., Heck R.F. J. Org. Chem. 40:1975;2667-2674.
27. Awad W.I., Ismail M.F., Kandile N.G. Austr. J. Chem. 28:1975;1621-1625.
28. Berthon L., Uguen D. Tetrahedron Lett. 26:1985;3975-3976.
29. Bakker B.H., Tjin A-Lim D.S., Van der Gen A. Tetrahedron Lett. 25:1984;4259-4262.
30. Couture A., Deniau E., Grandclaudon P. Tetrahedron Lett. 34:1993;1479-1482.
31. Cuevas J.-C., Patil P., Snieckus V. Tetrahedron Lett. 30:1989;5841-5844.
32. Palomo C., Aizpurua J.M., Legido M., Picard J.-P., Dunogues J., Constantieux T. Tetrahedron Lett. 33:1992;3903-3906.
33. Katritzky A.R., Yang Z., Lam J.N. J. Org. Chem. 56:1991;6917-6923.
34. Katritzky A.R., Yang Z., Lam J.N. J. Org. Chem. 58:1993;1970-1972. and references cited therein.
35. Katritzky A.R., Lang H., Lan X. Tetrahedron. 49:1993;2829-2838.
36. Katritzky A.R., Ignatchenko A.V., Lang H. J. Org. Chem. 60:1995;4002-4005.
37. Deniau E., Enders D. Tetrahedron. 57:2001;2581-2588.
38. Gregory R.M., Grieco P.A., Chidambaram V.S. J. Org. Chem. 46:1981;3761-3763.
39. McCombie S.W., Lin S.-I., Vice S.F. Tetrahedron Lett. 40:1999;8767-8770.
40. Beak P., Musick T.J., Liu C., Cooper T., Gallagher D.J. J. Org. Chem. 58:1993;7330-7335.
41. +, 27), 146 (34), 145 (100). IR (KBr) 1709 (CO).
42. 3 43.0.
43. +, 26), 220 (100), 219 (71). IR (KBr) 1702 (CO).