Tetrahedron

8-aryl-2-azabicyclo [3.3. 1] nonan-7-ones. Synthesis and retro-michael ring opening

J Bonjoch, J Quirante, D Solé, J Castells, M Galceran…

Index: Bonjoch, Josep; Quirante, Josefina; Sole, Daniel; Castells, Josep; Galceran, Montserrat; Bosch, Joan Tetrahedron, 1991 , vol. 47, # 25 p. 4417 - 4428

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Citation Number: 10

Abstract

The synthesis of 8-aryl-2-azabicyclo [3.3. 1] nonan-7-ones (7) by acid cyclization of 4-(3-aryl- 2-oxopropyl)-2-piperidinecarbonitriles (5) is reported. Bicyclic α-aril-β-amino ketones 7 easily undergo a retro-Michael ring opening to give the corresponding 2- arylcyclohexenones 8.

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