3a-(o-Nitrophenyl) octahydroindol-4-ones: Synthesis and spectroscopic analysis
D Solé, J Bosch, J Bonjoch
Index: Sole, Daniel; Bosch, Joan; Bonjoch, Josep Tetrahedron, 1996 , vol. 52, # 11 p. 4013 - 4028
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Citation Number: 18
Abstract
A short entry to 3a-(o-nitrophenyl) octahydroindol-4-ones employing ozonolysis and double reductive amination of 2-allyl-2-(o-nitrophenyl)-1, 3-cyclohexanedione (9) is described. The symmetric dione 9 is synthesized in a 50% overall yield from 1, 3-cyclohexanedione by means of o-nitroarylation followed by O-allylation and subsequent Claisen rearrangement. Configurational and conformational aspects of azabicyclic derivatives 1 (ak) are discussed.
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