PDF icon Download PDF
Synthesis 1996; 1996(7): 888-896
DOI: 10.1055/s-1996-4310
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

 PDF Download  Permissions and Reprints All articles of this category
Preview

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[6.3.0.01,5]undecanes in good to moderate yields together with 11-(arylimino)-3,4,4,9,9-pentaaryl-10-oxa-3-azatricyclo[6.3.0.01,5]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