The Huisgen Reaction of Azomethine Ylide to Isatins: A Facile Synthesis of Spiro-oxindoles

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

• 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 

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.