Abstract
A facile and convenient synthesis of spiro-oxindoles, structural units of many bioactive natural products, via 1,3-dipolar cycloaddition reaction of azomethine ylide with isatins is described.
Key words
ylides - isatins - indoles - heterocycles - spiro compounds
References 1 It is felt that in due recognition of the original contributions of Professor Rolf Huisgen in the development of 1,3-dipolar cycloadditions, which constitute a very important organic reaction, it is obligatory to call them Huisgen Reactions.
2a Kanemasa T.
Tsuge O.
Adv. Heterocycl. Chem.
1989,
45:
231
2b Tufariello JJ.
Meckler H.
Senaratana A.
Tetrahedron
1985,
41:
3447
3a Szántay C.
Blesko G.
Hongy K.
Dörnyei G. In The Alkaloids: Chemistry and Pharmacology
Vol. 27:
Brossi A.
Academic Press;
Orlando:
1986.
p.131
3b Szántay C.
Pure Appl. Chem.
1990,
62:
1299
4 Cordell GA. In
Heterocyclic Compounds: The Monoterpenoid Indole Alkaloids
Vol. 25:
Saxton JE.
Wiley;
New York:
1983.
Part 4.
p.539
5 The Alkaloids: Chemistry and Biology
Vol. 5:
Cordell GA.
Academic;
San Diego:
1998.
6a von Nussbaum F.
Danishefsky S.
Angew. Chem. Int. Ed.
2000,
112:
2259
6b Wang H.
Ganesan A.
J. Org. Chem.
2000,
65:
4685
6c Shebahar PR.
Williams RM.
J. Am. Chem. Soc.
2000,
122:
5666
6e Overman LE.
Rosen MD.
Angew. Chem. Int. Ed.
2000,
39:
4596
7 Palmisano G.
Annunziata R.
Papeo G.
Sisti GM.
Tetrahedron: Asymmetry
1996,
7:
1
8 Sebahar PR.
Usui T.
Williams RM.
Tetrahedron
2002,
58:
6311
9a Coulter T.
Grigg R.
Malone JF.
Sridharan V.
Tetrahedron Lett.
1991,
32:
5417
9b Fokas D.
Ryan WJ.
Casebier DS.
Coffen DL.
Tetrahedron Lett.
1998,
39:
2235
10 Nair V.
Sheela KC.
Rath NP.
Chem. Lett.
2000,
980
