Tetrahedron p. 1813 - 1816 (1980)
Update date:2022-09-26
Topics: Stereochemistry applications Mechanistic Studies Reaction Mechanism Catalysis Safety and Environmental Considerations Biological Activity
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The reductive cyclisation of 4,6-dimethyl and 4,6-dichloro derivatives of 3-hydroxy-2'-nitrodiphenyl ethers has been examined as a potential route to 1H-phenoxazinones. Unexpectedly, cyclisation of the dichloro compound proceeded with loss of a Cl and yielded 2-chloro-3H-phenoxazin-3-one. The cyclisation of a range of analogous substrates has been investigated and shown to provide novel and convenient syntheses of 3-amino-phenoxazine, 3H-phenothiazin-3-one and 8-hydroxy-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one.
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Doi:10.1021/jo01279a028
(1967)Doi:10.1016/0008-6215(94)00218-5
(1994)Doi:10.1016/S0040-4039(00)78647-3
(1980)Doi:10.1021/jo049344o
(2004)Doi:10.1023/B:RUGC.0000016014.90042.3b
(2003)Doi:10.1002/hlca.19840670312
(1984)
