e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

The Journal of Organic Chemistry

Quinone chemistry. Reaction of 2, 3-dichloro-1, 4-naphthoquinone with o-aminophenols under various conditions

NL Agarwal, W Schaefer

Index: Agarwal, Nand L.; Schaefer, Wolfram Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2155 - 2161

Full Text: HTML

Citation Number: 34

Abstract

5H-benzo [a] phenoxazin-5-one (7a), 2-amino-3H-phenoxazin-3-one (8) and triphenodioxazine (9a). Contradictory to earlier findings, 1 and 2a in MeOH/KOH afford 7a but the highest yield of the compound is achieved by using EtOH or MeQH and anhydrous potassium acetate. A probable mechanism for the formation of all reaction products is presented and detailed spectroscopic data of all compounds are given.

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

3-Amino-4-hydroxybenzoic acid Structure

3-Amino-4-hydro...

~61%

6-chloro-5-oxobenzo[a]phenoxazine-10-carboxylic acid Structure

6-chloro-5-oxob...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

2-Amino-4-methylphenol Structure

2-Amino-4-methy...

~84%

6-chloro-10-methylbenzo[a]phenoxazin-5-one Structure

6-chloro-10-met...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

2-Amino-4-methylphenol Structure

2-Amino-4-methy...

~2%

6-chloro-12a-hydroxy-9-methyl-5H-benzo[c]phenoxazin-5-one Structure

6-chloro-12a-hy...

6-chloro-12a-ethoxy-9-methyl-5H-benzo[c]phenoxazin-5-one Structure

6-chloro-12a-et...

Detail

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

Ethanol Structure

2-Amino-4-methylphenol Structure

2-Amino-4-methy...

~2%

6-chloro-12a-hydroxy-9-methyl-5H-benzo[c]phenoxazin-5-one Structure

6-chloro-12a-hy...

Detail

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

2-Amino-4-chlorophenol Structure

2-Amino-4-chlor...

~95%

6,10-dichlorobenzo[a]phenoxazin-5-one Structure

6,10-dichlorobe...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

2-Amino-4-chlorophenol Structure

2-Amino-4-chlor...

~3%

6,9-dichloro-12a-hydroxy-5H-benzo[c]phenoxazin-5-one Structure

6,9-dichloro-12...

(benzylamino)triphenylphosphonium bromide Structure

(benzylamino)tr...

Detail

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

Ethanol Structure

2-Amino-4-chlorophenol Structure

2-Amino-4-chlor...

~3%

6,9-dichloro-12a-hydroxy-5H-benzo[c]phenoxazin-5-one Structure

6,9-dichloro-12...

Detail

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

6-Amino-m-cresol Structure

6-Amino-m-cresol

~75%

6-chloro-9-methylbenzo[a]phenoxazin-5-one Structure

6-chloro-9-meth...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

2-Amino-4,6-dichlorophenol Structure

2-Amino-4,6-dic...

~88%

6,8,10-trichlorobenzo[a]phenoxazin-5-one Structure

6,8,10-trichlor...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

Phenol,2-amino-3,4,6-trichloro- Structure

Phenol,2-amino-...

~80%

6,8,10,11-tetrachlorobenzo[a]phenoxazin-5-one Structure

6,8,10,11-tetra...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

1-(2-Amino-3-hydroxyphenyl)ethanone Structure

1-(2-Amino-3-hy...

~76%

11-acetyl-6-chlorobenzo[a]phenoxazin-5-one Structure

11-acetyl-6-chl...

Quinone chemistry. Reaction of 2, 3-dichloro-1, 4-naphthoqui...

[Agarwal, Nand L.; Schaefer, Wolfram Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5144 - 5149]

Quinone chemistry. Reaction of 2, 3-dichloro-1, 4-naphthoqui...

[Agarwal, Nand L.; Schaefer, Wolfram Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5144 - 5149]