The reaction between 3-aminocrotonates and oxindole-3-ylidene derivatives: synthesis of highly substituted pyrroles |
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| Authors: | Stanley Rehn |
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| Affiliation: | Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park, SE-141 57 Huddinge, Sweden |
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| Abstract: | The reaction between 3-aminocrotonates and 3-acetonylideneoxindole in refluxing toluene resulted in 2-pyrrolo-3′-yloxindoles in high yields (around 90%). At room temperature the 2-pyrrolo-3′-yloxindoles exists as keto-enol tautomers. Treatment with POCl3 yielded the 2-chloro-3-pyrrolyl indole, which gave the pyrrolo annulated indolopyran-2-one upon basic hydrolysis of 2-chloro-3-pyrrolyl indole methyl ester. |
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| Keywords: | Pyrrole synthesis Keto-enol tautomers Indolopyrano-2-one |
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