581-30-6

Usage

Synthesis Reference(s)

Synthetic Communications, 20, p. 1543, 1990 DOI: 10.1080/00397919008052871

InChI:InChI=1/C12H7NOS/c14-8-5-6-10-12(7-8)15-11-4-2-1-3-9(11)13-10/h1-7H

Upstream product

• 92-84-2 10H-phenothiazine 
• 40248-84-8 3-mercaptophenol 
• 58-40-2 promazine 

Downstream Products

• 98412-06-7 2-m-Tolyloxy-phenothiazin-3-one 
• 98412-10-3 2-(4-Hydroxy-2-methyl-phenyl)-phenothiazin-3-one 
• 98412-09-0 2-hydroxyphenylphenothiazinone-3 
• 98412-05-6 2-Phenoxy-phenothiazin-3-one 
• 85833-59-6 2-Benzyloxy-phenothiazin-3-one 
• 1927-44-2 3-hydroxyphenothiazine 
• 98412-11-4 2-(4-acetoxyphenyl)phenothiazinone-3 
• 3568-81-8 thionol 
• 55847-60-4 7-(N-methyl-anilino)-phenothiazin-3-one 
• 55847-59-1 2-methylanilino-3H-phenothiazin-3-one 
• 68019-37-4 7-p-tolylsulfanyl-phenothiazin-3-one 
• 68019-38-5 2-p-tolylsulfanyl-phenothiazin-3-one 
• 27349-60-6 2-anilino-3H-phenothiazin-3-one 
• 55847-61-5 2,7-dianilino-phenothiazin-3-one 

Relevant academic research and scientific papers

Ozonization of phenothiazine and its analogues

When phenothiazine and phenoxazine were ozonized in dichloromethane, the cation radicals and the ozonate anion radicals were detected, whereas, in the ozonization of phenoxathiin and thianthrene, these radicals were not observed. Formation of these radicals was more favorable as greater was the polarity of the solvent and lower was the oxidation potential of the substrate. Ozonization of phenothiazine and phenoxazine in polar solvents was explained by the electron-transfer mechanism accompanied by the electrophilic ozone attack, and that of phenoxathiin and thianthrene by the electrophilic ozone attack alone.

Further studies on the cyclisation of 3-hydroxy-2'-nitrodiphenyl ethers and related compounds

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.