Synthesis 2004(13): 2103-2106  
DOI: 10.1055/s-2004-829200
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed One-Step Preparation of Novel Tricyclic Phenoxazine, Phenazine, and Dioxine Derivatives

Shinji Tanimori*, Yoshihiro Kato, Mitsunori Kirihata
Department of Applied Biochemistry, Graduate School of Agriculture and Life Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka 599-8531, Japan
Fax: +81(72)2549918; e-Mail: tanimori@biochem.osakafu-u.ac.jp;
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Publikationsverlauf

Received 19 April 2004
Publikationsdatum:
13. August 2004 (online)

Abstract

Reaction of cyclic meso allylic diacetates 5 and 6 with various 2-aminophenols, benzene-1,2-diamine, and benzene-1,2-diol in the presence of a palladium-phosphine catalyst gave novel phenoxazine, phenazine, and dioxine derivatives 7, 11, and 12 in moderate to excellent yields.

    References

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  • 4b cis-1,4-Diacetoxycyclohexene (6) was prepared from cyclohexa-1,3-diene by the palladium-catalyzed 1,4-diacetoxylation in 80% yield, see: Bäckvall J.-E. Bystrom SE. Nordberg RE. J. Org. Chem.  1984,  49:  4619 
  • 4c

    The palladium-catalyzed 1,4-diacetoxylation of cyclopentadiene gave low yield of 5 (<20%).

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