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Reaction of 1-arylmethylidenepyrazolidin-1-azomethine imines with aryl ketenes

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Abstract

A reaction of aryl ketenes with 1-arylmethylidenepyrazolidin-1-azomethine imines, generated by the diaziridine ring opening in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes catalyzed with Et2O·BF3, leads to 1,2-bis(phenylacetyl)pyrazolidine, 2-arylacetyl-1-arylidenepyrazolidin-1-ium chlorides, or a representative of 1,5-diazabicyclo[3.3.0]octan-2-ones, viz., 4-(4-eth-oxyphenyl)-3,3-diphenyl-1,5-diazabicyclo[3.3.0]octan-2-one, depending on the reaction conditions and the structure of the starting compounds. A mechanism suggested earlier for the transformation of 1,5-diazabicyclo[3.1.0]hexanes in the reaction with ketenes was confirmed.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    Yu. S. Syroeshkina, V. Yu. Petukhova, V. V. Kachala & N. N. Makhova

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Yu. V. Nelyubina

Authors
  1. Yu. S. Syroeshkina
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  2. V. Yu. Petukhova
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  3. V. V. Kachala
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  4. Yu. V. Nelyubina
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  5. N. N. Makhova
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Correspondence to N. N. Makhova.

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Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1401–1408, July, 2010.

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Syroeshkina, Y.S., Petukhova, V.Y., Kachala, V.V. et al. Reaction of 1-arylmethylidenepyrazolidin-1-azomethine imines with aryl ketenes. Russ Chem Bull 59, 1433–1441 (2010). https://doi.org/10.1007/s11172-010-0259-0

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  • DOI: https://doi.org/10.1007/s11172-010-0259-0

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