Manganese(III)-Mediated Oxidative Radical Cyclization 3. Synthesis of 3-Azabicyclo[3.3.0]-octan-2-ones and Related Compounds in the Reaction of 1,1,6,6-Tetraarylhexa-1,5-dienes with N,N’-Disubstituted Malonamides

Hiroshi Nishino; Kiyotaka Ishida; Hideaki Hashimoto; Kazu Kurosawa

doi:10.1055/s-1996-4310

Synthesis 1996; 1996(7): 888-896
DOI: 10.1055/s-1996-4310

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Manganese(III)-Mediated Oxidative Radical Cyclization 3. Synthesis of 3-Azabicyclo[3.3.0]-octan-2-ones and Related Compounds in the Reaction of 1,1,6,6-Tetraarylhexa-1,5-dienes with N,N’-Disubstituted Malonamides

Hiroshi Nishino^* , Kiyotaka Ishida, Hideaki Hashimoto, Kazu Kurosawa

^*Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860, Japan, Fax +81(96)3423320

Abstract

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The oxidation of 1,1,6,6-tetraarylhexa-1,5-dienes with manganese(III) acetate in the presence of N,N’-diarylmalonamides gave 1-(arylcarbamoyl)-8-(diarylmethylene)-3,4,4-triaryl-3-azabicyclo[3.3.0]octan-2-ones and 4,4,9,9-tetraaryl-2,11-bis(arlyimino)-3,10-dioxatricyclo[6.3.0.0^1,5]undecanes in good to moderate yields together with 11-(arylimino)-3,4,4,9,9-pentaaryl-10-oxa-3-azatricyclo[6.3.0.0^1,5]undecan-2-ones. A similar reaction in the presence of N,N’-dimethylmalonamide also yielded 3-azabicyclo[3.3.0]octan-2-one derivatives. An acid-catalyzed decomposition of the tricyclic diimines in acetic acid caused ring opening, while a similar decomposition in anhydrous THF resulted in recyclization at the nitrogen atom and/or hydrolysis of one of the imine bonds. A modification for the synthesis of 3-azabicyclo[3.3.0]octan-2-ones is discussed according to the results of the acid-catalyzed decomposition of the tricyclic imines.

manganese(III) acetate - oxidation - radical cyclization - 3-azabicyclo[3.3.0]octan-2-ones - 2,11-bis(imino)-3,10-dioxatricyclo[6.3.0.0]undecanes

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