Mechanism of the inverse-electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid |
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| Authors: | Michael De Rosa David Arnold |
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| Affiliation: | Department of Chemistry, The Pennsylvania State University Delaware County, 25 Yearsley Mill Road, Media, PA 19063, USA |
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| Abstract: | In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur. |
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| Keywords: | 2-Aminopyrroles Inverse-electron demand Diels-Alder Zwitterion intermediate Meisenheimer complex Cascade mechanism |
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