Lewis acid catalyzed reactions of donor-acceptor cyclopropanes with 1- and 2-pyrazolines: formation of substituted 2-pyrazolines and 1,2-diazabicyclo[3.3.0]octanes |
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Authors: | Yury V. Tomilov Roman A. Novikov Oleg M. Nefedov |
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Affiliation: | N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | The reaction of 2-substituted cyclopropane-1,1-dicarboxylates with 1- and 2-pyrazolines is efficiently catalyzed by scandium or ytterbium triflates to give N-substituted 2-pyrazolines or 1,2-diazabicyclo[3.3.0]octanes. The reactions of 2-pyrazolines give diazabicyclooctanes as the major products. In contrast, the reactions starting from 1-pyrazolines predominantly give N-substituted 2-pyrazolines, which become the major compounds obtained if an equimolar amount of GaCl3 is used. A possible reaction mechanism is suggested. |
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Keywords: | Cyclopropanedicarboxylates Pyrazolines 1,2-Diazabicyclo[3.3.0]octanes Lewis acid Catalysis |
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