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Paper | Regular issue | Vol 38, No. 2, 1994, pp.297-303
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6536
Cyclocondensation of β-Oxonitriles with Ketones or Aldehydes

Jean-François Stambach,* Louis Jung, and Raymond Hug

*Laboratoire de Chimie Thérapeutique, U.F.R. des Sciences Pharmaceutiques, Université Louis Pasteur, 74, route du Rhin, BP 24, 67401 ILLKIRCH Cedex, France


β-Oxonitriles (1) are easily condensed with cyclic ketones (2a-e) in anhydrous strong acidic conditions to give 1-oxa-5-azaspiro[5.5]undec-2-en-4-ones (3a-e). In the same manner acyclic ketones (2f,g) or aldehydes (2h,i) afford 2,3-dihydro-4H-1,3-oxazin-4-ones (3f-i). The mechanism of this cyclocondensation is discusssed.