Elsevier

Tetrahedron

Volume 58, Issue 15, 8 April 2002, Pages 3003-3007
Tetrahedron

Reaction of nitrile ylides with isatins and o-benzoquinones: formation of novel spirooxazoline derivatives

This paper is dedicated to the memory of Professor Josef (Gus) Fried who passed away on 7 August 2001
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Abstract

Nitrile ylide generated by the base catalysed reaction of imidoyl chlorides underwent dipolar cycloaddition with isatins, phenanthrenequinone and acenaphthenequinone to afford novel spirooxazoline derivatives.

Section snippets

Reactions of nitrile ylides with 1,2-quinones

In view of the encouraging results obtained with the nitrile ylides and isatins it was of interest to study the reaction of nitrile ylides with acenaphthenequinone and phenanthrenequinone. Thus when acenaphthenequinone 17 was allowed to react with imidoyl chlorides 1 and 2 in presence of triethylamine, products 18 and 19 were obtained (Scheme 2).

The products were purified by chromatography on a silica gel column, and characterized by spectroscopic analysis and single crystal X-ray analysis.16

Experimental

Various substituted isatins were prepared according to the literature procedure.17

Acknowledgements

D. S. thanks the CSIR New Delhi for financial assistance.

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