Synthetic and spectral studies of novel spiro {bicyclo[3,3,0]octene‐8,3′(2′H)‐indol}‐2′‐ones obtained from indol‐2,3‐diones

Abstract

The present article reports our approach toward the synthesis of spiro compounds via indol-2,3-diones. Thus, reaction of indol-2,3-dione derivatives with a secondary cyclic amino acid, namely, (R)-(−)-thiazolidine-4-carboxylic acid, affords a thiazolo-oxazolidinone as the main product. When the reaction is carried out in the presence of a dipolarophile, 1,3-dipolar cycloaddition to the intermediate azomethine ylide leads to a novel spiro compound. The products have been characterized on the basis of spectral studies, and the geometry of the intermediate iminium compound has been optimized by use of the semiempirical molecular orbital method. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 381–384, 1999