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Synlett 2000; 2000(7): 1034-1036
DOI: 10.1055/s-2000-6653
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Spirocyclopropanated Benzoazocinones and Tetrahydropyridones from Bicyclopropylidene by 1,3-Dipolar Cycloaddition/Rearrangement

Franca M. Cordero* , Ingrid Barile, Alberto Brandi, Sergei I. Kozhushkov, Armin de Meijere
  • *Dipartimento di Chimica Organica "U. Schiff", Centro di Studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni - C.N.R., Università di Firenze, via G. Capponi 9, I-50121 Firenze, Italy; E-mail: brandi@chimorg.unifi.it
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Publication Date:
31 December 2000 (online)

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1,3-Dipolar cycloaddition of N-aryl-C-phenylnitrones to bicyclopropylidene and subsequent thermal rearrangement afforded mixtures of spirocyclopropane-annelated tetrahydropyridones 12 and benzoazocinones 13 in good overall isolated yields (61-82%). The effect of para-substituents on the N-aryl ring has been found to be marginal.

bicyclopropylidene - cycloadditions - domino reactions - nitrones - rearrangements

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