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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 12
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Original Articles

Facile Synthesis of Spiro Oxindoles, Azaoxindoles, and Dihydroisoquinolone

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Pages 1742-1751 | Received 29 Jan 2010, Published online: 29 Apr 2011
 

Abstract

Formation of 1-aryl-4-oxo-cyclohexa(e)nonecarboxylates from the Diels–Alder cycloaddition of 2-trimethylsilyloxy-1,3-butadiene and Danishefsky diene with aryl- and pyridylacrylates and further conversion thereof to spirocycles is described. This provides an efficient method for spiro oxindoles, azaoxindoles, and dihydroisoquinolones.

ACKNOWLEDGMENTS

The authors acknowledge Dr. Francisco Talamas and Dr. Josh Taygerly for their valuable input and the analytical department for providing the spectroscopic and physical data.

Notes

a All are isolated yields and are not optimized.

b Hydrogenation in the presence of Pd-C and subsequent treatment with Zn/AcOH was required for the formation of 1c.

c An inseparable mixture of the desired product and a side product with 16 mass units higher was obtained.

d None of the desired spirocycle was formed.

a All are isolated yields and are not optimized.

Current name and affiliation for Christa Parmer: Christa Tatyosian, Bio-Rad Laboratories, Hercules, California, USA.

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