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Synthesis 2004(13): 2103-2106
DOI: 10.1055/s-2004-829200
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
Further Information
Received
19 April 2004
Publication Date:
13 August 2004 (online)
Publication History
Publication Date:
13 August 2004 (online)
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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.
Key words
tandem reaction - palladium catalyst - allylic substitution - phenoxazine - meso compound
- 1
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4a
cis-1,4-Diacetoxycyclopentene (5) was prepared from cyclopentadiene by the photosensitized oxygenation followed by acetylation in 41% yield, see:
Kaneko C.Sugimoto A.Tanaka S. Synthesis 1974, 876 -
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%).
- 5
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