Synthesis and Chemical Transformations of Acridone-9
Abstract
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.
About the Authors
L. M. Mironovich
Southwest State University
Russian Federation
Russian Federation
Lyudmila M. Mironovich, Dr. of Sci. (Chemistry), Professor, Professor of the Department of Fundamental Chemistry and Chemical Technology
50 Let Oktyabrya str. 94, Kursk 305040
S. A. Antonova
Southwest State University
Russian Federation
Russian Federation
Svetlana А. Antonova, Undergraduate of the Department of Fundamental Chemistry and Chemical Technology
50 Let Oktyabrya str. 94, Kursk 305040
References
1. Deeva E. G., Pavlovskaya Yа. V., Kiselev O. I. Strukturno-funktsional'nyi analiz biologicheskoi aktivnosti proizvodnykh akridina [Structural and functional analysis of the biological activity of acridine derivatives]. Vestnik Rossijskoj akademii medicinskih nauk = Bulletin of the Russian Academy of Medical Sciences, 2004, no. 2, pp. 29–34.
2. Gorelik M. V. Himiya antrahinonov i ih proizvodnyh [Chemistry of anthraquinones and their derivatives]. Moscow, Himiya Publ., 1983. 204 р.
3. Rubcov M. V., Bajchikov A. G. Sinteticheskie himiko-farmacevticheskie preparaty [Synthetic chemical and pharmaceutical preparations]. Moscow, Medicina Publ., 1971. 331 р.
4. Burov Yu. V., Goncharenko S. B., Robakidze T. N., Portnov Yu. N., Kadyshe- va L. V., Penke I. H., Peganov E. M., Suhanova S. A., Tananova G. V., Voronin A. E., Kotlobaj A. A., Oshis Ya. F., Pchelinceva L. E. Proizvodnye 9-aminoakridina ili ih soli s organicheskimi ili neorganicheskimi kislotami, proyavlyayushchie psihotropnuyu, antiamnesticheskuyu i lipidreguliruyushchuyu aktivnost' [9-Aminoacridine derivatives or their salts with organic or inorganic acids that exhibit psychotropic, antiamnestic and lipid-regulating activity]. Patent RF, no. 2024509, 1994.
5. Kamal A., Olepu S., Poddutoori R., Gujjar R., Pogula P. K. С8-Linked pyrrolo[2,1C][1,4]benzodiazepineacridone/acridine hybrids. Patent US, no. 0222132, 2005.
6. Markovich Yu. D., Pelevin N. A., Akimova N. S., Klimova L. G., Kudryavceva T. N., Muhacheva E. S., Gubin T. I. Poluchenie akridon-2-sul'fokisloty i izuchenie ee antimikrobnoj aktivnosti [Obtaining acridone-2-sulfonic acid and studying its antimicrobial activity]. Izvestiya Kurskogo gosudarstvennogo tekhnicheskogo universiteta = Proceedings of the Kursk State Technical University, 2007, no. 1 (18), pp. 35–39.
7. Goshaev M. S., Otryshchenko O. S., Sadykov A. S. Reakciya Ul'mana [Ullman's reaction]. Uspekhi himii = Advances in Chemistry, 1972, vol. XLI, is. 12, pp. 2198–2223.
8. Matsumura K. Sulfonation of 6-Nitroacridone. Journal of the American Chemical Society, 1938, vol. 60, no. 3, pp. 593–595.
9. Stepanov B. I. Vvedenie v himiyu i tekhnologiyu organicheskih krasitelej [Introduction to chemistry and technology of organic dyes]. Moscow, Himiya Publ., 1984. 592 р.
10. Barton D., Ollis U. D. Obshchaya organicheskaya himiya. Azotosoderzhashchie cikly [General organic chemistry. Nitrogen-containing cycles]. Moscow, Himiya Publ., 1985. 752 p.
11. Mironovich L. M., Ageeva L. S., Podol'nikova A. Yu. Nukleofil'noe zameshchenie hlora v 9-hlorakridine amino(gidrazino, tiokso) – 1,2,4-triazinami [Nucleophilic substitution of chlorine in 9-chloracridine with amino (hydrazino, thioxo) - 1,2,4-triazines]. Zhurnal obshchej himii = Journal of General Chemistry, 2016, vol. 86, is. 2, pp. 343–345.
12. Kudryavceva T. N., Bogatyrev K. V., Sysoev P. I., Klimova L. G. Sintez i antibakterial'naya aktivnost' novyh N9-zameshchennyh akridin-9-aminov [Synthesis and antibacterial activity of new N9-substituted acridine-9-amines]. Zhurnal obshchej himii = Journal of General Chemistry, 2019, vol. 89, no. 1, pp. 148–151.
13. Mironovich L. M., Podol'nikova A. Yu. Sintez 3-[(akrid-9-on-10-il)metil]-5-R-6-R1,2,4-triazinov [Synthesis of 3 - [(acrid-9-on-10-il)methyl] - 5-R-6-R-1,2,4-triazines]. Zhurnal obshchej himii = Journal of General Chemistry, 2015, vol. 85, no. 10, pp. 1740–1741.
14. Lamanov A. Yu., Kudryavceva T. N. Sintez novyh proizvodnyh akridina s ftorsoderzhashchim 1,2,4- i 1,3,4-oksadiazol'nym fragmentom [Synthesis of new acridine derivatives with a fluorinated 1,2,4 - and 1,3,4-oxadiazole fragment]. Ftornye zametki = Fluoride Notes, 2015, no. 2 (99). URL: http://www.hotes.fluorine1.ru/public/99_1_ru.pdf. (accessed 23.11.2020)
15. Mironovich L. M., Sigaeva N. N., Makarova T. A., Lysenko A. V. Sintez proizvodnyh akridina v usloviyah mikrovolnovogo izlucheniya [Synthesis of acridine derivatives under microwave radiation]. Izvestiya Yugo-Zapadnogo gosudarstvennogo universiteta. Seriya: Tekhnika i tekhnologii = Proceedings of the Southwest State University. Series: Engineering and Technologies, 2016, vol. 2(19), pp. 191–196.
16. Shchepina N. E., Avrorina V. V., Badun G. A., L'yuis S. B., Uhanov S. E. Poluchenie kondensirovannyh n-fenilzameshchyonnyh piridinievyh proizvodnyh reakciej pryamogo fenilirovaniya nukleogennymi fenil-kationami [Preparation of condensed n-phenyl-substituted pyridinium derivatives by direct phenylation with nucleogenic phenyl cations]. Himiya geterociklicheskih soedinenij = Chemistry of heterocyclic compounds, 2012, no. 2, pp. 320–327.
17. Kudryavceva T. N., Lamanov A. Yu., Klimova L. G., Nazarov G. V. Sintez i antibakterial'naya aktivnost' efirov 9-okso-9,10-digidroakridinkarbonovyh kislot, soderzhashchih triazol'nyj fragment [Synthesis and antibacterial activity of esters of 9-oxo-9,10-dihydro-acridine-carboxylic acids containing a triazole fragment]. Zhurnal obshchej himii = Journal of General Chemistry , 2018, vol. 88, is. 4, pp. 593–598.
18. Kudryavceva T. N., Lamanov A.Yu., Klimova L. G., Nazarov G. V. Sintez i antimikrobnaya aktivnost' proizvodnyh akridinkarbonovyh kislot, soderzhashchih piperazinovyj fragment [Synthesis and antimicrobial activity of acridine carboxylic acid derivatives containing piperazine fragment]. Izvestiya Akademii nauk. Seriya: himicheskaya = Izvestiya Akademii nauk. Series: Chemical, 2017, no. 1, pp. 123–128.
19. Fan X., You J., Kang J., Oua Q., Zhu Q. New reagents for determination of amino acids by liquid chromatography with pre-column uorescence derivatization. Analytica Chimica Acta, 1998, vol. 367, pp. 81–91.
20. Prech E., Byulmann F., Affolter K. Opredelenie stroeniya organicheskikh soedinenij. Tablits spektralnykh dannykh [Determination of the structure of organic compounds. Tables of spectral data]. Moscow, Mir Publ., Binom. Laboratoriya znanij Publ., 2012. 438 р.
21. Vartanyan R. S. Sintez osnovnykh lekarstvennykh sredstv [Synthesis of basic medicines]. Moscow, Meditsinskoe informatsionnoe agentstvo Publ., 2004. 845 р.
Review
For citations:
Mironovich L.M., Antonova S.A. Synthesis and Chemical Transformations of Acridone-9. Proceedings of the Southwest State University. Series: Engineering and Technology. 2021;11(1):134-145. (In Russ.)
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