A new synthetic procedure to spiro[cyclohexane-1,3′-indoline]-2′,4-diones

✍ Scribed by Egle Maria Beccalli; Francesca Clerici; Maria Luisa Gelmi

• Book ID: 104205327
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 193 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)00627-6

✦ Synopsis

A new synthetic pathway to spiro[cyclohexane-1,3 0 -indoline]-2 0 ,4-diones was found starting from 3-chloromethylene-2-indolones 1 and Danishefsky's diene 2. Their synthesis consists of several steps involving the formation of the cycloadducts, the 6-chloro-4-trimethylsilyloxy-2-methoxyspiro[cyclohex-3-en-1,3 0 -indolin]-2 0 -one derivatives, transformed into spiro[cyclohexa-2,5-dien-1,3 0 -indoline]-2 0 ,4-diones via 6-chloro-spiro[cyclohex-2-en-1,3 0 -indoline]-2 0 ,4-dione intermediates. The reduction of spiro[cyclohexa-2,5dien-1,3 0 -indoline]-2 0 ,4-diones gave spiro[cyclohexane-1,3 0 -indoline]-2 0 ,4-diones 7. Using a 'one pot reaction', starting from 1 and 2, compounds 7 were obtained in satisfactory overall yield.