A new synthetic procedure to spiro[cyclohexane-1,3′-indoline]-2′,4-diones |
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Authors: | Egle Maria BeccalliFrancesca Clerici Maria Luisa Gelmi |
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Affiliation: | Istituto di Chimica Organica ‘Alessandro Marchesini’, Facoltà di Farmacia, Università di Milano, Via Venezian 21, I-20133 Milano, Italy |
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Abstract: | A new synthetic pathway to spiro[cyclohexane-1,3′-indoline]-2′,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′-indolin]-2′-one derivatives, transformed into spiro[cyclohexa-2,5-dien-1,3′-indoline]-2′,4-diones via 6-chloro-spiro[cyclohex-2-en-1,3′-indoline]-2′,4-dione intermediates. The reduction of spiro[cyclohexa-2,5-dien-1,3′-indoline]-2′,4-diones gave spiro[cyclohexane-1,3′-indoline]-2′,4-diones 7. Using a ‘one pot reaction’, starting from 1 and 2, compounds 7 were obtained in satisfactory overall yield. |
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Keywords: | Diels-Alder oxoindolinylidenes spiroindolenines phenanthridinone |
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