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Synthesis 1997; 1997(1): 53-56
DOI: 10.1055/s-1997-1507
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A Facile Cyclopropane Ring-Formation by the Thermal Reaction of 2-(Alk-2-enylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxaldehydes with Tosylhydrazine

Bin Sun, Kenji Adachi, Michihiko Noguchi*
  • *Department of Applied Chemistry, Faculty of Engineering, Yamaguchi University, Tokiwadai, Ube 755, Japan
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Publication Date:
31 December 2000 (online)

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A facile intramolecular cyclopropane ring formation was accomplished by the reaction of heterocyclic aldehydes bearing alkenylamino moieties with tosylhydrazine in less polar solvents. The thermally induced isomerization of hydrazone to azomethine imine and its intramolecular cycloaddition reaction leading to a pyrazolodine derivative was suggested as a key step for the cyclopropane ring formation.

hydrazone-azomethine imine isomerization - tosylhydrazone - 1,3-dipolar cycloaddition - 1-pyrazoline - cyclopropanation

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