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Synfacts 2007(12): 1240-1240
DOI: 10.1055/s-2007-991394
DOI: 10.1055/s-2007-991394
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Pyrazolidines via GaCl3-Catalyzed Insertion of Diazines into Cyclopropanes
V. S. Korotkov, O. V. Larionov, A. Hofmeister, J. Magull, A. de Meijere*
Georg-August-Universität Göttingen, Germany
Further Information
Publication History
Publication Date:
22 November 2007 (online)
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Significance
A facile synthesis of pyrazolidines by reaction of cyclopropane 1,1-diesters and alkyl and ester diazines is reported. The yields are modest and regiochemically selective insertion of the diazine (when R2 ∂ R3) is not achieved. Use of cis-diazines (4-phenyl-1,2,4-triazoline-3,5-dione) resulted in mixtures of pyrazolidines with major C-1-C-2 insertion products. The mechanism proposed involves GaCl3-catalyzed ring opening of the cyclopropane ring followed by insertion of the diazine. Investigation of the mechanism produced no conclusive evidence.