Synthesis and Chemical Transformations of Acridone-9
Purpose. To study condensation reactions as a method for obtaining compounds of the acridine series and to investigate their reactivity. Methods. We used the techniques and methods of organic chemistry in the synthesis of new derivatives of the acridine series. The purity of the products was controlled using the chromatographic method of analysis, and the structure was confirmed by a set of spectral methods of analysis on the instrument base of the Department of Fundamental Chemistry and Chemical Technology of the South-Western State University. Results. N-acridoneacetic acid was isolated by cyclization of N, N-diphenylglycine-2-carboxylic acid while boiling in concentrated sulfuric acid. The cyclization of N,N-diphenylglycine-2-carboxylic acid, subject to the use of phosphorus chloroxide and phosphorus trichloride as a cyclizing agent, which is widely used in organic synthesis to obtain substituted 9-chloroacridine, bypassing the step of obtaining acridone-9, led to nucleophilic substitution of hydroxy residues on halogen with the release of 2[(2-chloro-2-oxoethyl)phenylamino] benzoyl chloride. It was found that the closure of the cycle to the corresponding 2-(9-chloroacridin-10 (9H)-yl) acetyl chloride does not proceed. 2- (9-Oxoacridin-10-yl) acetyl chloride was obtained in high yield by refluxing 2-(9-oxoacridin-10-yl)acetic acid in thionyl chloride in the absence of solvent. Substitution of the oxo group for halogen under the experimental conditions does not occur due to the structure of the starting acridine. Substitution of hydrazine for the chlorine atom in the acid chloride by refluxing it with 84% hydrazine hydrate led to 2-(9-oxoacridin-10-yl)acetohydrazide in high yield. The structure of the compounds was proved using spectral methods of analysis. Conclusion. 2-(9-Oxoacridin-10-yl)acetyl chloride was synthesized by the reaction of thionyl chloride with 2-(9-oxoacridin-10-yl)acetic acid, on the basis of which a promising laboratory method for the preparation of 2-(9-oxoacridin-10-yl)acetohydrazide.